Apoptosis signal-regulating kinase 1 inhibitors

1. A method of inhibiting ASK1 enzyme in a subject, the method comprising administering to the subject a compound of the formula:

or a pharmaceutically acceptable salt thereof, wherein the subject suffers from a disease selected from the group consisting of ischemia/reperfusion in stroke, heart attacks, myocardial ischemia, organ hypoxia, vascular hyperplasia, cardiac hypertrophy, hepatic ischemia, liver disease, congestive heart failure, and thrombin-induced platelet aggregation;

R 2 is selected from the group consisting of nitro, cyano, thio, carbonyloxy, (C 1-10 )alkoxy, (C 4-12 )aryloxy, hetero(C 1-10 )aryloxy, carbonyl, aminocarbonyl, amino, (C 1-10 )alkylamino, sulfonamido, imino, (C 1-10 )alkyl, halo(C 2-10 )alkyl, hydroxy(C 1-10 )alkyl, carbonyl(C 1-10 )alkyl, thiocarbonyl(C 1-10 )alkyl, sulfonyl(C 1-10 )alkyl, sulfinyl(C 1-10 )alkyl, (C 1-10 )azaalkyl, (C 1-10 )oxaalkyl, (C 1-10 )oxoalkyl, imino(C 1-10 )alkyl, (C 3-12 )cycloalkyl(C 1-5 )alkyl, hetero(C 3-12 )cycloalkyl(C 1-10 )alkyl, aryl(C 1-10 )alkyl, hetero(C 1-10 )aryl(C 1-5 )alkyl, (C 9-12 )bicycloaryl(C 1-5 )alkyl, hetero(C 8-12 )bicycloaryl(C 1-5 )alkyl, hetero(C 1-10 )alkyl, (C 3-12 )cycloalkyl, hetero(C 3-12 )cycloalkyl, (C 9-12 )bicycloalkyl, hetero(C 3-12 )bicycloalkyl, (C 4-12 )aryl, hetero(C 1-10 )aryl, (C 9-12 )bicycloaryl, and hetero(C 4-12 )bicycloaryl, each unsubstituted or substituted with 1-3 substituents, provided that R 2 is not an unsubstituted n-(C 1-3 )alkyl;

R 3 is selected from the group consisting of hydrogen, halo, nitro, cyano, thio, hydroxy, carbonyloxy, (C 1-10 )alkoxy, (C 4-12 )aryloxy, hetero(C 1-10 )aryloxy, carbonyl, aminocarbonyl, amino, (C 1-10 )alkylamino, sulfonamido, imino, (C 1-10 )alkyl, halo(C 1-10 )alkyl, hydroxy(C 1-10 )alkyl, carbonyl(C 1-10 )alkyl, thiocarbonyl(C 1-10 )alkyl, sulfonyl(C 1-10 )alkyl, sulfinyl(C 1-10 )alkyl, (C 1-10 )azaalkyl, (C 1-10 )oxaalkyl, (C 1-10 )oxoalkyl, imino(C 1-10 )alkyl, (C 3-12 )cycloalkyl(C 1-5 )alkyl, hetero(C 3-12 )cycloalkyl(C 1-10 )alkyl, aryl(C 1-10 )alkyl, hetero(C 1-10 )aryl(C 1-5 )alkyl, (C 9-12 )bicycloaryl(C 1-5 )alkyl, hetero(C 8-12 )bicycloaryl(C 1-5 )alkyl, hetero(C 1-10 )alkyl, (C 3-12 )cycloalkyl, hetero(C 3-12 )cycloalkyl, (C 9-12 )bicycloalkyl, hetero(C 3-12 )bicycloalkyl, (C 4-12 )aryl, hetero(C 1-10 )aryl, (C 9-12 )bicycloaryl, and hetero(C 4-12 )bicycloaryl, each unsubstituted or substituted with 1-2 substituents; and

R 4 is selected from the group consisting of (C 3-12 )cycloalkyl, hetero(C 3-12 )cycloalkyl, (C 9-12 )bicycloalkyl, hetero(C 3-12 )bicycloalkyl, (C 4-12 )aryl, hetero(C 1-10 )aryl, (C 9-12 )bicycloaryl, and hetero(C 4-12 )bicycloaryl, each unsubstituted or substituted with 1-3 substituents,

where

each of said 1-3 substituents of R 2 is independently selected from the group consisting of halo, nitro, cyano, oxo, hydroxy, thio, thio(C 1-6 )alkyl, arylalkyloxy, carbonyloxy, (C 1-10 )alkoxy, (C 4-12 )aryloxy, hetero(C 1-10 )aryloxy, aminocarbonyloxy, carbonyl, (C 1-6 )alkylcarbonyl, amino, amido, carboxamido, (C 1-10 )alkylamino, methylcarbonylamino, sulfonamido, imino, (C 1-6 )alkylsulfonyl, (C 1-10 )alkyl, halo(C 1-10 )alkyl, hydroxy(C 1-10 )alkyl, carbonyl(C 1-10 )alkyl, thiocarbonyl(C 1-10 )alkyl, sulfonyl(C 1-10 )alkyl, sulfinyl(C 1-10 )alkyl, (C 1-10 )azaalkyl, (C 1-10 )oxaalkyl, (C 1-10 )oxoalkyl, imino(C 1-10 )alkyl, (C 3-12 )cycloalkyl(C 1-5 )alkyl, hetero(C 3-12 )cycloalkyl(C 1-10 )alkyl, aryl(C 1-10 )alkyl, hetero(C 1-10 )aryl(C 1-5 )alkyl, (C 9-12 )bicycloaryl(C 1-5 )alkyl, hetero(C 8-12 )bicycloaryl(C 1-5 )alkyl, hetero(C 1-10 )alkyl, (C 3-12 )cycloalkyl, hetero(C 3-12 )cycloalkyl, (C 9-12 )bicycloalkyl, hetero(C 3-12 )bicycloalkyl, (C 4-12 )aryl, hetero(C 1-10 )aryl, (C 9-12 )bicycloaryl, and hetero(C 4-12 )bicycloaryl;

each of said 1-2 substituents of R 3 is independently selected from the group consisting of hydroxy, halo, halo(C 1-6 )alkyl, (C 1-6 )alkyl, (C 3-6 )cycloalkyl, hetero(C 1-5 )cycloalkyl, phenyl, and hetero(C 1-5 )aryl;

each of said 1-3 substituents of R 4 is independently selected from the group consisting of halo, nitro, cyano, oxo, thio, mercapto, hydroxy, carbonyloxy, (C 1-10 )alkoxy, (C 4-12 )aryloxy, hetero(C 1-10 )aryloxy, carbonyl, (C 1-10 )alkoxycarbonyl, (C 4-12 )aryloxycarbonyl, hetero(C 1-10 )aryloxycarbonyl, amino, amido, carboxamido, carbamoyl, (C 1-10 )alkylamino, sulfonamido, sulfamoyl, imino, phosphonyl, (C 1-10 )alkyl, halo(C 1-10 )alkyl, hydroxy(C 1-10 )alkyl, carbonyl(C 1-10 )alkyl, thiocarbonyl(C 1-10 )alkyl, sulfonyl(C 1-10 )alkyl, sulfinyl(C 1-10 )alkyl, phosphonyl(C 1-10 )alkyl, (C 1-10 )azaalkyl, (C 1-10 )oxaalkyl, (C 1-10 )oxoalkyl, imino(C 1-10 )alkyl, (C 3-12 )cycloalkyl(C 1-5 )alkyl, hetero(C 3-12 )cycloalkyl(C 1-10 )alkyl, aryl(C 1-10 )alkyl, hetero(C 1-10 )aryl(C 1-5 )alkyl, (C 9-12 )bicycloaryl(C 1-5 )alkyl, hetero(C 8-12 )bicycloaryl(C 1-5 )alkyl, hetero(C 1-10 )alkyl, (C 3-12 )cycloalkyl, hetero(C 3-12 )cycloalkyl, (C 9-12 )bicycloalkyl, hetero(C 3-12 )bicycloalkyl, (C 4-12 )aryl, hetero(C 1-10 )aryl, (C 9-12 )bicycloaryl, and hetero(C 4-12 )bicycloaryl.

2. The method according to claim 1 , wherein R 4 is selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, piperidinyl, piperazinyl, morpholinyl, and admantanyl, each unsubstituted or substituted with said 1-3 substituents.

3. The method according to claim 1 , wherein R 4 is selected from the group consisting of phenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl, each unsubstituted or substituted with said 1-3 substituents.

4. The method according to claim 3 , wherein at least one of said 1-3 substituents is

where R 21 is selected from the group consisting of hydroxyl, (C 1-4 )alkyl, —CF 3 , —(CH 2 )OH, —(CH 2 )CN, —(CH 2 )C(O)OH, —(CH 2 )CONH 2 , —(CH 2 )NH 2 , —(CH 2 )NHC(O)C(O)OH, —(CH 2 )C(O)OCH 3 , —O(CH 2 )CH(OH)CH 2 OH, —(CH 2 ) n aryl, —O(CH 2 ) n aryl, —(CH 2 ) n heteroaryl, —O(CH 2 ) n heteroaryl, where n is 0, 1, 2, 3, or 4.

5. The method according to claim 1 , wherein R 4 is selected from the group consisting of:

6. The method according to claim 1 , wherein R 4 is selected from the group consisting of:

7. The method according to claim 1 , wherein R 4 is selected from the group consisting of:

8. The method according to claim 1 , wherein R 4 is an unsubstituted or substituted phenyl of the formula:

where

R 7 , R 8 , R 9 , R 10 , and R 11 are each independently selected from the group consisting of hydrogen, halo, hydroxyl, nitro, thio, cyano, (C 1-6 )alkyl, (C 2-6 )alkenyl, (C 2-6 )alkynyl, halo(C 1-6 )alkyl, (C 1-6 )alkoxy, hydroxyl(C 1-6 )alkyl, phosphonylalkyl, mercapto, sulfamoyl, amino, amido, carboxamido, carbamoyl, carbonyl, carbonyloxy, hetero(C 1-5 )aryl, and (C 4-6 )aryl, and each unsubstituted or substituted; provided at least two of R 7 , R 8 , R 9 , R 10 , and R 11 are hydrogen.

9. The method according to claim 8 , wherein R 7 , R 8 , R 9 , R 10 , and R 11 are each independently selected from the group consisting of hydrogen, hydroxyl, nitro, fluoro, chloro, bromo, cyano, (C 1-6 )alkoxy, —OCHF 2 , —OCF 3 , furanyloxy, (C 1-6 )alkyl, halo(C 1-6 )alkyl, hydroxyl(C 1-6 )alkyl, —CH 2 NHC(O)OC(CH 3 ) 3 , —C(CH 3 )(OH)CF 3 , hetero(C 1-5 )aryl(C 1-6 )alkyl, —C(CH 3 )═NOH, —CH 2 OCH 2 CF 3 , —NC(O)CH 3 , —NHS(O) 2 CH 3 , —N(CH 3 ) 2 , —C(O)OCH 3 , —OCH(CH 3 ) 2 , —SCF 3 , -sulfonylpyrrolidinyl, hetero(C 1-5 )aryl, hetero(C 1-5 )cycloalkyl,

where

k is 1, 2, 3, or 4; and

R 21 is selected from the group consisting of —(CH 2 ) n OH, —C(O)OH, —C(O)OCH 3 , cyano, —(CH 2 ) n NH 2 , —(CH 2 ) n NHC(O)C(O)OH, —(CH 2 ) n C(O)OH, —(CH 2 ) n C(O)OCH 3 , (C 1-4 )alkyl, halo(C 1-4 )alkyl, —(CH 2 ) n CN, —(CH 2 ) n CONH 2 , —(CH 2 ) n aryl, —(CH 2 ) n heteroaryl, —O(CH 2 ) n aryl, —O(CH 2 ) n heteroaryl, and —O(CH 2 ) n CH(OH)CH 2 OH, where n is 0, 1, 2, 3, or 4.

10. The method according to claim 9 , wherein R 21 is selected from the group consisting of cyano, hydroxyl, methyl, perfluoromethyl, hydroxylmethyl, —CH 2 NH 2 , —(CH 2 )C(O)OH, —(CH 2 )C(O)OCH 3 , —(CH 2 )NHC(O)C(O)OH, —OCH 2 CH(OH)CH 2 OH, and —O(CH 2 ) n heteroaryl where n is 1 or 2.

11. The method according to claim 8 , wherein R 9 is independently selected from the group consisting of hydrogen, tert-butyl, —CF 3 , —C(CH 3 )(OH)CF 3 , —C(CH 3 ) 2 CF 3 , —C(CH 3 ) 2 OH, —C(CH 3 ) 2 (CH 2 OH), —C(O)OCH 3 ,

—C(CH 3 ) 2 (OCH 2 CH(OH)CH 2 OH), —C(CH 3 ) 2 CN, —C(CH 3 ) 2 CH 2 CN, —C(CH 3 ) 2 O(CH 2 ) n heteroaryl where n is 1 or 2, and R 7 , R 8 , R 10 , and R 11 are each hydrogen.

12. The method according to claim 1 , wherein R 4 is selected from the group consisting of:

where n is 0, 1, 2 3 or 4.

13. The method according to claim 1 , wherein R 2 is selected from the group consisting of (C 3-12 )cycloalkyl, hetero(C 3-12 )cycloalkyl, (C 9-12 )bicycloalkyl, hetero(C 3-12 )bicycloalkyl, (C 4-12 )aryl, hetero(C 1-10 )aryl, (C 9-12 )bicycloaryl, and hetero(C 4-12 )bicycloaryl, each unsubstituted or substituted with said 1-3 substituents.

14. The method according to claim 13 , wherein R 2 is selected from the group consisting of furanyl, thienyl, pyrrolyl, pyrrolidinyl, oxazolyl, thiazolyl, imidazolyl, pyrazolyl, triazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, phenyl, pyridyl, pyrazinyl, pyrimidinyl, pyranyl, thiopyranyl, tetrahydrothiopyranyl, piperidinyl, piperazinyl, pyridazinyl, triazinyl, indolyl, isoindolyl, indolizinyl, benzimidazolyl, purinyl, naphthalenyl, quinolinyl, isoquinolinyl, cinnolinyl, phthalazinlyl, quinazolinyl, quinoxalinyl, naphthyridinyl, pteridinyl, morpholino, thiomorpholinyl, cyclohexyl, cyclopentyl, cyclohexenyl, and cyclopentenyl, each unsubstituted or substituted with said 1-3 substituents.

15. The method according to claim 13 , wherein R 2 is selected from the group consisting of:

each of which is unsubstituted or substituted with said 1-3 substituents, wherein R is hydrogen or is one of said 1-3 substituents.

16. The method according to claim 13 , wherein R 2 is a phenyl, unsubstituted or substituted with said 1-3 substituents.

17. The method according to claim 13 , wherein R 2 is morpholinyl, unsubstituted or substituted with said 1-3 substituents.

18. The method according to claim 1 , wherein R 2 is unsubstituted phenyl.

19. The method according to claim 1 , wherein R 3 is selected from the group consisting of hydrogen, (C 1-6 )alkyl, (C 1-6 )haloalkyl, (C 1-6 )cycloalkyl, and (C 1-6 )alkoxy, each unsubstituted or substituted with said 1-2 substituents.

20. The method according to claim 1 , wherein the compound has the formula:

or is a pharmaceutically acceptable salt thereof,

wherein

t is 0, 1, 2 or 3; and

each R 30 is independently selected from the group consisting of hydroxy, nitro, halo, cyano, oxo, (C 1-6 )alkoxy, (C 4-6 )aryloxy, (C 4-6 )aryl(C 1-6 )alkoxy, (C 1-6 )alkyl, (C 1-6 )haloalkyl, hydroxy(C 1-6 )alkyl, aminocarbonyl(C 1-6 )alkyl, cyanoalkyl, (C 1-6 )haloalkoxy, thio, thio(C 1-6 )alkyl, amino, sulfonylamino, (C 1-6 )alkylamino, (C 1-6 )alkylsulfonylamino, amido, aryl, aryl(C 1-6 )alkyl, (C 1-6 )alkylcarbonyl, (C 1-6 )alkoxycarbonyl, carboxamido, hydroxycarbonyl, and (C 1-6 )alkylsulfonyl.

21. The method according to claim 20 , wherein R 4 is selected from the group consisting of:

22. The method according to claim 20 , wherein R 4 is selected from the group consisting of:

where n is 0, 1, 2, 3 or 4.

23. The method according to claim 20 , wherein each R 30 is independently selected from the group consisting of hydroxyl, nitro, cyano, fluoro, chloro, methyl, cyanomethyl, —CH 2 OCH 3 , isobutyl, CF 3 , —CH 2 OH, —(CH 2 ) 2 OH, —(CH 2 ) 3 OH, —CH(CH 3 )CH 2 OH, —OCF 3 , isopropyloxy, —OCH 2 C(O)OH, benzyloxy, —OCH 2 C(O)OCH 2 CH 3 , —OCH 2 CH 2 N(CH 3 ) 2 , —OCH 2 CH 2 -morpholinyl, —OCH 2 CH 2 OCH 3 , —C(O)CH 3 , —C(O)NH 2 , —NHC(O)CH 3 , —NHS(O) 2 CH 3 , —N(CH 3 ) 2 , —SCH 3 , —S(O) 2 CH 3 , and phenyl.

24. The method according to claim 20 , wherein t is 0.

25. The method according to claim 20 , wherein R 3 is selected from the group consisting of hydrogen, (C 1-6 )alkyl, (C 1-6 )haloalkyl, (C 1-6 )cycloalkyl, and (C 1-6 )alkoxy, each unsubstituted or substituted with said 1-2 substituents.

26. The method according to claim 1 , wherein the compound has the formula:

or is a pharmaceutically acceptable salt thereof, and

R 21 is selected from the group consisting of —(CH 2 ) n OH, —C(O)OH, —C(O)OCH 3 , cyano, —(CH 2 ) n NH 2 , —(CH 2 ) n NHC(O)C(O)OH, —(CH 2 ) n C(O)OH, —(CH 2 ) n C(O)OCH 3 , (C 1-4 alkyl, halo(C 1-4 )alkyl, —(CH 2 ) n CN, —(CH 2 ) n CONH 2 , —(CH 2 ) n aryl, —(CH 2 ) n heteroaryl, —O(CH 2 ) n aryl, —O(CH 2 ) n heteroaryl, and —O(CH 2 ) n CH(OH)CH 2 OH, where n is 0, 1, 2, 3, or 4.

27. The method according to claim 26 , wherein R 21 is selected from the group consisting of cyano, hydroxyl, methyl, perfluoromethyl, hydroxylmethyl, —CH 2 NH 2 , —(CH 2 )NHC(O)C(O)OH, —(CH 2 )C(O)OH, —(CH 2 )C(O)OCH 3 , —O(CH 2 ) n heteroaryl where n is 1 or 2, and —OCH 2 CH(OH)CH 2 OH.

28. The method according to claim 26 , wherein R 21 is OH.

29. The method according to claim 26 , wherein R 2 is selected from the group consisting of:

30. The method according to claim 26 , wherein R 2 is unsubstituted phenyl.

31. The method according to claim 26 , wherein R 3 is selected from the group consisting of hydrogen, (C 1-6 )alkyl, (C 1-6 )haloalkyl, (C 1-6 )cycloalkyl, and (C 1-6 )alkoxy, each unsubstituted or substituted with said 1-2 substituents.

32. The method according to claim 1 , wherein the compound is selected from the group consisting of:

4-tert-butyl-N-(7-(3-(hydroxymethyl)phenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(thiophen-2-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-(tert-butyl)-N-(7-(3-(3-hydroxypropyl)phenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(4-fluoro-3-(hydroxymethyl)phenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(3-(hydroxymethyl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

N-(7-(3-(hydroxymethyl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

N-(7-(3-(hydroxymethyl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(1,1,1-trifluoro-2-hydroxypropan-2-yl)benzamide;

4-tert-butyl-N-(7-(4-(methylsulfonyl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(4-methoxyphenyl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(3-(2-hydroxyethyl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(3-(3-hydroxypropyl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

N-(7-(3-acetylphenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-tert-butylbenzamide;

4-tert-butyl-N-(7-(6-methoxypyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

N-(7-(6-acetamidopyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-tert-butylbenzamide;

4-tert-butyl-N-(7-(3-methoxyphenyl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-(2-hydroxypropan-2-yl)-N-(7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-(2-hydroxypropan-2-yl)-N-(7-(3-(methylsulfonamido)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

N-(7-(furan-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

4-(2-hydroxypropan-2-yl)-N-(7-(4-methoxyphenyl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-(2-hydroxypropan-2-yl)-N-(7-p-tolylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

N-(7-(3-(cyanomethyl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

N-(7-(4-carbamoylphenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

4-(2-hydroxypropan-2-yl)-N-(7-(4-(methylthio)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-(2-hydroxypropan-2-yl)-N-(7-(4-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

N-(7-(3-acetamidophenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

ethyl 2-(3-(5-(4-(2-hydroxypropan-2-yl)benzamido)pyrazolo[1,5-a]pyrimidin-7-yl)phenoxy)acetate;

2-(3-(5-(4-(2-hydroxypropan-2-yl)benzamido)pyrazolo[1,5-a]pyrimidin-7-yl)phenoxy)acetic acid;

4-(2-hydroxypropan-2-yl)-N-(7-(3-(methoxymethyl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-(1-hydroxy-2-methylpropan-2-yl)-N-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-(1-hydroxy-2-methylpropan-2-yl)-N-(7-(3-(hydroxymethyl)phenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-(1-hydroxy-2-methylpropan-2-yl)-N-(7-(3-(methoxymethyl)phenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-[7-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide;

4-tert-butyl-N-[7-(4-tert-butylphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide;

4-tert-butyl-N-{7-[3-(cyanomethyl)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl}benzamide;

4-tert-butyl-N-(7-(furan-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-p-tolylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(4-cyanophenyl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(3,5-dimethylphenyl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(4-chlorophenyl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(2-chlorophenyl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(4-carbamoylphenyl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(4-(methylthio)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

N-(7-(benzo[b]thiophen-2-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-tert-butylbenzamide;

4-tert-butyl-N-(7-(2,4-dimethoxyphenyl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(3-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(4-(trifluoromethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-o-tolylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(2-(hydroxymethyl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

N-(7-(2-acetamidophenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-tert-butylbenzamide;

N-(7-(biphenyl-2-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-tert-butylbenzamide;

4-tert-butyl-N-(7-(2-(methylsulfonamido)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(2-methoxypyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(naphthalen-2-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(3-nitrophenyl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(4-nitrophenyl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(3,4-difluorophenyl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(4-sec-butylphenyl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(isoquinolin-4-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(4-isobutyl-3-nitrophenyl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(2-formylphenyl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(3-(methylsulfonamido)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

N-(7-(1-benzyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-tert-butylbenzamide;

N-(7-(3,4-dihydroisoquinolin-2(1H)-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

4-tert-butyl-N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(3,4-dihydroisoquinolin-2(1H)-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

(S)—N-(7-(2-(hydroxymethyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

(R)—N-(7-(2-(hydroxymethyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

(R)-4-(2-hydroxypropan-2-yl)-N-(7-(3-hydroxypyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

(S)-4-(2-hydroxypropan-2-yl)-N-(7-(3-hydroxypyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

N-(7-(4-(2-hydroxyethyl)piperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

4-(2-hydroxypropan-2-yl)-N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

N-(7-(4-hydroxypiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

N-(7-(2-(2-hydroxyethyl)piperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

(S)-4-tert-butyl-N-(7-(3-hydroxypiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

(R)—N-(7-(3-hydroxypiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

(R)-4-tert-butyl-N-(7-(3-hydroxypiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

(S)—N-(7-(3-hydroxypiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

N-(7-(6,7-dihydro-1H-pyrazolo[4,3-a]pyridin-5(4H)-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

4-(2-hydroxypropan-2-yl)-N-(7-(2-methylpiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-(2-hydroxypropan-2-yl)-N-(7-(3-methylpiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

N-(7-(3,5-dimethylpiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

(R)-1-(5-(4-(2-hydroxypropan-2-yl)benzamido)pyrazolo[1,5-a]pyrimidin-7-yl)piperidine-3-carboxamide;

(R)-1-(5-(4-(2-hydroxypropan-2-yl)benzamido)pyrazolo[1,5-a]pyrimidin-7-yl)piperidine-3-carboxylic acid;

(S)-1-(5-(4-(2-hydroxypropan-2-yl)benzamido)pyrazolo[1,5-a]pyrimidin-7-yl)piperidine-3-carboxamide;

(S)-1-(5-(4-(2-hydroxypropan-2-yl)benzamido)pyrazolo[1,5-a]pyrimidin-7-yl)piperidine-3-carboxylic acid;

4-(2-hydroxypropan-2-yl)-N-(7-(pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

N-(7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

4-(2-hydroxypropan-2-yl)-N-(7-(4-oxo-3,4,7,8-tetrahydropyrido[4,3-d]pyrimidin-6(5H)-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-(2-hydroxypropan-2-yl)-N-(7-(4-(methylsulfonyl)piperazin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

N-(7-(5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

(S)-1-(5-(4-(2-hydroxypropan-2-yl)benzamido)pyrazolo[1,5-a]pyrimidin-7-yl)pyrrolidine-2-carboxamide;

4-(2-hydroxypropan-2-yl)-N-(7-(5-oxo-1,4-diazepan-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-(1-hydroxy-2-methylpropan-2-yl)-N-(2-methyl-7-(pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

(S)-4-(1-hydroxy-2-methylpropan-2-yl)-N-(7-(2-(hydroxymethyl)pyrrolidin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

(R)-ethyl 1-(5-(4-(1-hydroxy-2-methylpropan-2-yl)benzamido)-2-methylpyrazolo[1,5-a]pyrimidin-7-yl)piperidine-3-carboxylate;

4-(1-hydroxy-2-methylpropan-2-yl)-N-(7-(3-hydroxyazetidin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-(1-hydroxy-2-methylpropan-2-yl)-N-(2-methyl-7-(4-oxo-3,4,7,8-tetrahydropyrido[4,3-d]pyrimidin-6(5H)-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-(1-hydroxy-2-methylpropan-2-yl)-N-(2-methyl-7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

(R)-4-(1-hydroxy-2-methylpropan-2-yl)-N-(7-(3-hydroxypyrrolidin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-(1-hydroxy-2-methylpropan-2-yl)-N-(7-(4-(2-hydroxyethyl)piperidin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(piperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

1-(5-(4-tert-butylbenzamido)pyrazolo[1,5-a]pyrimidin-7-yl)piperidine-3-carboxamide;

4-tert-butyl-N-(7-(2-(2-hydroxyethyl)piperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(octahydroisoquinolin-2(1H)-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(4-hydroxy-4-phenylpiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(4-methylpiperazin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(4-phenethylpiperazin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(6,7-dihydro-2H-pyrazolo[4,3-c]pyridin-5 (4H)-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

(S)-4-tert-butyl-N-(7-(2-(hydroxymethyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(4-hydroxypiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(3-hydroxypiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

1-(5-(4-tert-butylbenzamido)pyrazolo[1,5-a]pyrimidin-7-yl)piperidine-4-carboxamide;

N-(7-(3-acetamidopyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-tert-butylbenzamide;

4-tert-butyl-N-(7-(4-(2-hydroxyethyl)piperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

1-(5-(4-tert-butylbenzamido)pyrazolo[1,5-a]pyrimidin-7-yl)piperidine-3-carboxylic acid;

4-tert-butyl-N-(7-(3-hydroxypyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

(R)—N-(7-(3-acetamidopyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-tert-butylbenzamide;

N-(7-(1H-imidazol-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-tert-butylbenzamide;

N-(7-(1H-1,2,4-triazol-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-tert-butylbenzamide;

4-tert-butyl-N-(7-(6,7-dihydro-1H-pyrazolo[4,3-b]pyridin-4(5H)-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

(E)-4-tert-butyl-N-(7-(2-cyclohexylvinyl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(dimethylamino)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

N-(7-(benzyl(2-(dimethylamino)ethyl)amino)pyrazolo[1,5-a]pyrimidin-5-yl)-4-tert-butylbenzamide;

4-(1-hydroxy-2-methylpropan-2-yl)-N-(2-methyl-7-(methyl(phenethyl)amino)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-[7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide;

4-tert-butyl-N-{7-[(4-methoxybenzyl)amino]pyrazolo[1,5-a]pyrimidin-5-yl}benzamide;

4-tert-butyl-N-{7-[(1-methyl-1-phenylethyl)amino]pyrazolo[1,5-a]pyrimidin-5-yl}benzamide;

4-tert-butyl-N-[7-(phenylamino)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide;

4-tert-butyl-N-(7-(isobutylamino)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(butylamino)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(tert-butylamino)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(3-hydroxypropylamino)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(cyclopentylamino)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(furan-2-ylmethylamino)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

N-(7-(2-acetamidoethylamino)pyrazolo[1,5-a]pyrimidin-5-yl)-4-tert-butylbenzamide;

4-tert-butyl-N-(7-(2-isopropoxyethylamino)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(3-(methylthio)propylamino)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

N-(7-(benzylamino)pyrazolo[1,5-a]pyrimidin-5-yl)-4-tert-butylbenzamide;

4-tert-butyl-N-(7-(cyclohexylmethylamino)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(phenethylamino)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

N-(7-(3-amino-3-oxopropylamino)pyrazolo[1,5-a]pyrimidin-5-yl)-4-tert-butylbenzamide;

4-tert-butyl-N-(7-(3-fluorobenzylamino)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(2,3-dihydro-1H-inden-2-ylamino)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(4-hydroxyphenethylamino)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(2-phenoxyethylamino)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(3-(2-oxopyrrolidin-1-yl)propylamino)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

N-(7-(benzo[d][1,3]dioxol-5-ylmethylamino)pyrazolo[1,5-a]pyrimidin-5-yl)-4-tert-butylbenzamide;

N-(7-(2-(1H-indol-3-yl)ethylamino)pyrazolo[1,5-a]pyrimidin-5-yl)-4-tert-butylbenzamide;

4-tert-butyl-N-(7-(4-(trifluoromethyl)benzylamino)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(3,4-dimethoxyphenethylamino)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(4-sulfamoylbenzylamino)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

N-(7-(3,5-bis(trifluoromethyl)benzylamino)pyrazolo[1,5-a]pyrimidin-5-yl)-4-tert-butylbenzamide;

4-tert-butyl-N-(7-(2-methoxyethylamino)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(pentan-3-ylamino)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

N-(7-(2-amino-2-oxoethylamino)pyrazolo[1,5-a]pyrimidin-5-yl)-4-tert-butylbenzamide;

4-tert-butyl-N-(7-(3-methylbenzylamino)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(2-(dimethylamino)ethylamino)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(pyridin-3-ylmethylamino)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(2-(pyridin-2-yl)ethylamino)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-((5-methylpyrazin-2-yl)methylamino)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

N-(7-(3-(1H-imidazol-1-yl)propylamino)pyrazolo[1,5-a]pyrimidin-5-yl)-4-tert-butylbenzamide;

N-(7-(2-(1H-imidazol-5-yl)ethylamino)pyrazolo[1,5-a]pyrimidin-5-yl)-4-tert-butylbenzamide;

(5)-methyl 2-(5-(4-tert-butylbenzamido)pyrazolo[1,5-a]pyrimidin-7-ylamino)-3-(1H-imidazol-5-yl)propanoate;

4-tert-butyl-N-(7-(2-hydroxycyclohexylamino)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(pyridin-2-ylamino)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(pyridin-3-ylamino)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(pyrimidin-2-ylamino)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

N-(7-(3-(benzyloxy)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

N-(7-(2,3-dihydrobenzofuran-5-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

4-(2-hydroxypropan-2-yl)-N-(7-(3-methoxyphenyl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

(E)-4-(2-hydroxypropan-2-yl)-N-(7-styrylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-(2-hydroxypropan-2-yl)-N-(7-(thiophen-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

N-(7-(3-hydroxyazetidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

4-(2-hydroxypropan-2-yl)-N-(7-(2-methylpyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

N-(7-(3-fluoropyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

4-(2-hydroxypropan-2-yl)-N-(7-(3-oxopiperazin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

N-(7-(3-cyanopiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

4-(2-hydroxypropan-2-yl)-N-(7-(3-methyl-4-oxopiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

N-(7-(3,3-dimethylpiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

N-(7-(4-formylpiperazin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

(S)—N-(7-(3-(dimethylamino)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

(R)-4-(2-hydroxypropan-2-yl)-N-(7-(2-(methoxymethyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

(R)—N-(7-(3-(dimethylamino)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

N-(7-(2,5-dimethylpiperazin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

4-(2-hydroxypropan-2-yl)-N-(7-(4-methyl-1,4-diazepan-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

N-(7-(2,6-dimethylmorpholino)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

N-(7-(3-(hydroxymethyl)piperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

N-(7-(4-(hydroxymethyl)piperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

4-(2-hydroxypropan-2-yl)-N-(7-(4-methoxypiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-(2-hydroxypropan-2-yl)-N-(2-methyl-7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-(2-hydroxypropan-2-yl)-N-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

(R)-4-(2-hydroxypropan-2-yl)-N-(7-(3-hydroxypyrrolidin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-(2-hydroxypropan-2-yl)-N-(2-methyl-7-(piperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

N-(7-(benzo[d][1,3]dioxol-4-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

4-(2-hydroxypropan-2-yl)-N-(2-methyl-7-(4-oxo-3,4,7,8-tetrahydropyrido[4,3-d]pyrimidin-6(5H)-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-(2-hydroxypropan-2-yl)-N-(2-methyl-7-thiomorpholinopyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-[5-({[4-(1-hydroxy-1-methylethyl)phenyl]carbonyl}amino)-2-methylpyrazolo[1,5-a]pyrimidin-7-yl]thiomorpholin-1-ium-1-olate;

N-[7-(1,1-dioxidothiomorpholin-4-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(1-hydroxy-1-methylethyl)benzamide;

N-(7-(4-(ethylsulfonyl)piperazin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

N-(7-(4-(hydroxymethyl)piperidin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

N-(2-methyl-7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)-6-(trifluoromethyl)nicotinamide;

N-(2-methyl-7-(4-oxo-3,4,7,8-tetrahydropyrido[4,3-d]pyrimidin-6(5H)-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-6-(trifluoromethyl)nicotinamide;

N-(2-cyclopropyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

N-(2-cyclopropyl-7-(3-(hydroxymethyl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

N-(2-cyclopropyl-7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

N-(2-cyclopropyl-7-(4-hydroxypiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

methyl 4-(7-chloro-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-ylcarbamoyl)benzoate;

4-(2-hydroxypropan-2-yl)-N-(7-(4-(2-hydroxypropan-2-yl)piperidin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-(2-hydroxypropan-2-yl)-N-(7-(4-methoxyphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide.

4-(2-hydroxypropan-2-yl)-N-(7-morpholino-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-(2-hydroxypropan-2-yl)-N-(7-(4-(methoxymethyl)piperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-(2-hydroxypropan-2-yl)-N-(7-(4-(2-hydroxypropan-2-yl)piperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

N-(7-(2,3-dihydrobenzofuran-5-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

methyl 4-(7-phenyl-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-ylcarbamoyl)benzoate;

4-(2-hydroxypropan-2-yl)-N-(7-(4-(methoxymethyl)piperidin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

1-(5-(4-(2-hydroxypropan-2-yl)benzamido)-2-methylpyrazolo[1,5-a]pyrimidin-7-yl)piperidine-4-carboxylic acid;

N-(2-ethyl-7-(4-methoxyphenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

N-(2-ethyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

4-(2-hydroxypropan-2-yl)-N-(7-phenyl-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

N-(2-ethyl-7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

N-(7-(benzo[d][1,3]dioxol-5-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

N-(7-(4-(1-hydroxy-2-methylpropyl)piperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

N-(7-(4-formyl-1,4-diazepan-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

N-(7-(4-acetyl-1,4-diazepan-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

4-(2-hydroxypropan-2-yl)-N-(7-(3-hydroxypyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

N-(7-(4-acetyl-1,4-diazepan-1-yl)-2-ethylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

methyl 1-(5-(4-(2-hydroxypropan-2-yl)benzamido)-2-methylpyrazolo[1,5-a]pyrimidin-7-yl)piperidine-4-carboxylate;

4-(2-hydroxypropan-2-yl)-N-(7-(3-methoxyphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

N-(7-(4-(1-hydroxy-2-methylpropyl)piperidin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

4-(2-hydroxypropan-2-yl)-N-(2-methyl-7-(1-oxo-2,8-diazaspiro[4.5]decan-8-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-(2-hydroxypropan-2-yl)-N-(2-methyl-7-(4-(pyrrolidine-1-carbonyl)piperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

N-(7-(benzo[d][1,3]dioxol-5-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

1-(5-(4-(2-hydroxypropan-2-yl)benzamido)pyrazolo[1,5-a]pyrimidin-7-yl)piperidine-4-carboxylic acid;

Methyl 1-(5-(4-(2-hydroxypropan-2-yl)benzamido)pyrazolo[1,5-a]pyrimidin-7-yl)piperidine-4-carboxylate;

4-(2-hydroxypropan-2-yl)-N-(2-methyl-7-(4-(phenylthio)piperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-(2-hydroxypropan-2-yl)-N-(2-methyl-7-(4-(phenylsulfonyl)piperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-(2-hydroxypropan-2-yl)-N-(2-methyl-7-(4-(phenylsulfonyl)piperazin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

N-(7-(4-(N,N-dimethylsulfamoyl)piperazin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

4-(2-hydroxypropan-2-yl)-N-(2-methyl-7-(4-(propylsulfonyl)piperazin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-(2-hydroxypropan-2-yl)-N-(2-methyl-7-(4-(methylsulfonyl)-1,4-diazepan-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-(2-hydroxypropan-2-yl)-N-(7-(1,2,3,4-tetrahydroisoquinolin-7-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

1-(5-(4-(2-hydroxypropan-2-yl)benzamido)-2-methylpyrazolo[1,5-a]pyrimidin-7-yl)piperidine-4-carboxamide;

4-(2-hydroxypropan-2-yl)-N-(2-methyl-7-(4-methylpiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-(2-hydroxypropan-2-yl)-N-(2-methyl-7-(1,4-oxazepan-4-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

N-(7-(4-formyl-1,4-diazepan-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

N-(7-(4-acetyl-1,4-diazepan-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

(S)—N-(7-(2-(hydroxymethyl)pyrrolidin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

N-ethyl-1-(5-(4-(2-hydroxypropan-2-yl)benzamido)-2-methylpyrazolo[1,5-a]pyrimidin-7-yl)piperidine-4-carboxamide;

1-(5-(4-(2-hydroxypropan-2-yl)benzamido)-2-methylpyrazolo[1,5-a]pyrimidin-7-yl)-N-methylpiperidine-4-carboxamide;

1-(5-(4-(2-hydroxypropan-2-yl)benzamido)-2-methylpyrazolo[1,5-a]pyrimidin-7-yl)-N,N-dimethylpiperidine-4-carboxamide;

N-(7-(2,2-difluorobenzo[d][1,3]dioxol-4-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

N-(7-(4,4-difluoropiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

4-(2-hydroxypropan-2-yl)-N-(7-(4-(trifluoromethyl)piperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-(2-hydroxypropan-2-yl)-N-(2-methyl-7-(1,2,3,4-tetrahydroisoquinolin-7-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

1-(5-(4-(2-hydroxypropan-2-yl)benzamido)pyrazolo[1,5-a]pyrimidin-7-yl)-N-methylpiperidine-4-carboxamide;

1-(5-(4-(2-hydroxypropan-2-yl)benzamido)pyrazolo[1,5-a]pyrimidin-7-yl)-N-isopropylpiperidine-4-carboxamide;

(R)-1-(5-(4-(2-hydroxypropan-2-yl)benzamido)pyrazolo[1,5-a]pyrimidin-7-yl)-N-methylpiperidine-3-carboxamide;

(R)-1-(5-(4-(2-hydroxypropan-2-yl)benzamido)pyrazolo[1,5-a]pyrimidin-7-yl)-N,N-dimethylpiperidine-3-carboxamide;

4-(2-hydroxypropan-2-yl)-N-(7-phenoxypyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

(R)-1-(5-(4-(2-hydroxypropan-2-yl)benzamido)pyrazolo[1,5-a]pyrimidin-7-yl)-N-isopropylpiperidine-3-carboxamide;

N-(7-(3-fluoropyrrolidin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

N-(7-(4-(2-hydroxyethyl)piperidin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

N-(7-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)-4-(6-oxo-1,6-dihydropyridin-3-yl)benzamide;

(E)-4-(2-hydroxypropan-2-yl)-N-(2-methyl-7-styrylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

(E)-N-(7-(4-fluorostyryl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

(E)-4-(2-hydroxypropan-2-yl)-N-(7-(3-methoxystyryl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

N-(7-(4-acetamidopiperidin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

(R)—N-ethyl-1-(5-(4-(2-hydroxypropan-2-yl)benzamido)pyrazolo[1,5-a]pyrimidin-7-yl)piperidine-3-carboxamide;

N-(7-(4-chlorophenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

N-(7-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

4-(furan-3-yl)-N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

methyl 1-(4-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-ylcarbamoyl)phenyl)cyclopropanecarboxylate;

N-(7-butoxypyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

methyl 1-(4-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-ylcarbamoyl)phenyl)cyclopropanecarboxylate;

1-(4-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-ylcarbamoyl)phenyl)cyclopropanecarboxylic acid;

4-(2-hydroxypropan-2-yl)-N-(7-methoxypyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

N-(7-(5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

N-(7-(3,4-dimethoxyphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

N-(7-(3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

N-(7-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

N-(7-(4-(2-hydroxyethyl)piperidin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-2-phenylcyclopropanecarboxamide;

N-(7-(benzo[b]thiophen-5-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

4-(2-hydroxypropan-2-yl)-N-(2-methyl-7-(4-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-(2-hydroxypropan-2-yl)-N-(7-(4-isopropoxyphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

(S)—N-(7-(3-acetamidopyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

(R)—N-(7-(3-acetamidopyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

N-(7-((S)-3-fluoropyrrolidin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-2-phenylcyclopropanecarboxamide;

N-(7-((R)-3-fluoropyrrolidin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-2-phenylcyclopropanecarboxamide;

N-(7-(4-methoxyphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-2-phenylcyclopropanecarboxamide;

(S)-1-(5-(4-(2-hydroxypropan-2-yl)benzamido)pyrazolo[1,5-a]pyrimidin-7-yl)-N-methylpiperidine-3-carboxamide;

(S)—N-(7-(3-acetamidopiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

(S)—N-(7-(3-aminopiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

(R)—N-(7-(3-acetamidopiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

N-(7-(4-chlorophenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

N-(7-(4-fluoro-3-methoxyphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

(R)—N-(7-(3-aminopiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

5-(2-hydroxypropan-2-yl)-N-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)picolinamide;

N-(7-(5-chlorothiophen-2-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

N-(7-(4-acetamidopiperidin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-2-phenylcyclopropanecarboxamide;

N-(7-(3-fluoro-4-methoxyphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

N-(7-(3-chloro-4-methoxyphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

6-(2-hydroxypropan-2-yl)-N-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)nicotinamide;

6-(2-hydroxypropan-2-yl)-N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)nicotinamide;

(R)-1-(5-(4-(2-hydroxypropan-2-yl)benzamido)-2-methylpyrazolo[1,5-a]pyrimidin-7-yl)-N-methylpiperidine-3-carboxamide;

N-(7-(4-chloro-3-methylphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

N-(7-(3-chloro-4-hydroxyphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

N-(7-(4-(2-(dimethylamino)ethoxy)phenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

4-(2-hydroxypropan-2-yl)-N-(2-methyl-7-(4-(2-morpholinoethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-(2-hydroxypropan-2-yl)-N-(7-(4-(2-methoxyethoxy)phenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-(2-hydroxypropan-2-yl)-N-(2-methyl-7-(4-propionamidopiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-(2-hydroxypropan-2-yl)-N-(2-methyl-7-(4-ureidopiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

N-(7-(4-(2-amino-2-oxoethyl)piperidin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

N-(7-(benzofuran-5-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

N-(7-(3-(dimethylamino)phenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

4-(2-hydroxypropan-2-yl)-N-(7-(6-hydroxypyridin-3-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-(2-hydroxypropan-2-yl)-N-(7-(6-methoxypyridin-3-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

3,3-dimethyl-N-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)-2,3-dihydrobenzofuran-6-carboxamide;

N-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)-2-(pyridin-4-yl)cyclopropanecarboxamide;

N-(7-(4-(cyclopropanecarboxamido)piperidin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

4-(2-cyanopropan-2-yl)-N-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-(1-amino-2-methylpropan-2-yl)-N-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

2-(2-methyl-2-(4-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-ylcarbamoyl)phenyl)propylamino)-2-oxoacetic acid;

N-(7-(4-acetamidopiperidin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-2-(pyridin-4-yl)cyclopropanecarboxamide;

N-(2-methyl-7-(4-ureidopiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-2-(pyridin-4-yl)cyclopropanecarboxamide;

6-(2-hydroxypropan-2-yl)-N-(7-(4-methoxyphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)nicotinamide;

N-(7-(benzo[d][1,3]dioxol-5-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-6-(2-hydroxypropan-2-yl)nicotinamide;

N-(7-(2,3-dihydrobenzofuran-5-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-6-(2-hydroxypropan-2-yl)nicotinamide;

N-(7-(4-acetamidopiperidin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-6-(2-hydroxypropan-2-yl)nicotinamide;

6-(2-hydroxypropan-2-yl)-N-(2-methyl-7-(4-ureidopiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)nicotinamide;

N-(7-(4-(2-amino-2-oxoethyl)piperazin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

methyl 3-methyl-3-(4-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-ylcarbamoyl)phenyl)butanoate;

(1S,2S)—N-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)-2-phenylcyclopropanecarboxamide;

(1R,2R)—N-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)-2-phenylcyclopropanecarboxamide;

(1R,2S)—N-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)-2-phenylcyclopropanecarboxamide;

N-(7-(4-chloro-3-methoxyphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

N-(2-methyl-7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)-4-(trifluoromethoxy)benzamide;

N-(2-hydroxyethyl)-1-(5-(4-(2-hydroxypropan-2-yl)benzamido)-2-methylpyrazolo[1,5-a]pyrimidin-7-yl)piperidine-3-carboxamide;

N-(7-(6-ethoxypyridin-3-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

4-(2-hydroxypropan-2-yl)-N-(7-(6-isopropoxypyridin-3-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

N-(7-(6-(cyclopropylmethoxy)pyridin-3-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide;

N-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(trifluoromethylthio)benzamide;

(1R,2R)—N-(7-(4-acetamidopiperidin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-2-phenylcyclopropanecarboxamide;

(1R,2R)—N-(2-methyl-7-(4-ureidopiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-2-phenylcyclopropanecarboxamide;

(1S,2S)—N-(7-(4-acetamidopiperidin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-2-phenylcyclopropanecarboxamide;

2-(4-fluorophenyl)-N-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)cyclopropanecarboxamide;

cis-2-(4-fluorophenyl)-N-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)cyclopropanecarboxamide;

N-(7-(4-acetamidopiperidin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-2-(4-fluorophenyl)cyclopropanecarboxamide;

2-(4-fluorophenyl)-N-(2-methyl-7-(4-ureidopiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclopropanecarboxamide;

N-(2-methyl-7-(4-ureidopiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(trifluoromethoxy)benzamide;

N-(7-(4-(2-amino-2-oxoethyl)piperidin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(trifluoromethoxy)benzamide;

N-(7-(4-acetamidopiperidin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(trifluoromethoxy)benzamide;

N-(7-(4-acetamidopiperidin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-2-(pyridin-4-yl)cyclopropanecarboxamide;

N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)cyclopropanecarboxamide;

N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)cyclopentanecarboxamide;

tert-butyl 4-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-ylcarbamoyl)piperidine-1-carboxylate;

N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)cyclobutanecarboxamide;

trans-N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)-2-phenylcyclopropane carboxamide;

4-cyano-N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

2,4-difluoro-N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)-1H-indole-2-carboxamide;

N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)-1H-indole-6-carboxamide;

N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)-1-naphthamide;

methyl 4-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-ylcarbamoyl)benzoate;

N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)biphenyl-4-carboxamide;

2,4-dimethyl-N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

1-hydroxy-N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)-2-naphthamide;

4-methyl-N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

3-methyl-N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

2-methoxy-N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)-2-naphthamide;

4-bromo-N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)-1H-imidazole-4-carboxamide;

N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)nicotinamide;

N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)picolinamide;

N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)pyrazine-2-carboxamide;

N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)quinoline-2-carboxamide;

N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)iso quinoline-1-carboxamide;

1-(3-bromophenyl)-3,5-dimethyl-N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)-1H-pyrazole-4-carboxamide;

N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)-1-((3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-8-yl)methyl)piperidine-3-carboxamide;

diethyl 4-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-ylcarbamoyl)benzylphosphonate;

tert-butyl 4-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-ylcarbamoyl)benzylcarbamate;

N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)-4-(thiophen-2-yl)benzamide;

4-(5-methyl-1H-tetrazol-1-yl)-N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)-4-(oxazol-5-yl)benzamide;

4-morpholino-N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-(1H-imidazol-1-yl)-N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)-4-(3-oxo-3,4-dihydro-2H-1,4-thiazin-5-yl)benzamide;

N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)-4-(3-(trifluoromethyl)-1H-pyrazol-1-yl)benzamide;

2,2-difluoro-N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)benzo[d][1,3]dioxole-4-carboxamide;

4-(2-methylthiazol-4-yl)-N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

N,2-dimethyl-N-(4-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-ylcarbamoyl)phenyl)benzamide;

4((2,4-dioxothiazolidin-5-yl)methyl)-N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

3-(1H-benzo[d]imidazol-2-yl)-N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

7-methoxy-2,2-dimethyl-N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)-2,3-dihydrobenzofuran-4-carboxamide;

4-(5-methyl-1,2,4-oxadiazol-3-yl)-N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)-4-(1,2,3-thiadiazol-4-yl)benzamide;

(E)-4-(1-(hydroxyimino)ethyl)-N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-(furan-2-yl)-N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(1-oxo-thiomorpholino)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(methyl(1,1-dioxo(tetrahydro-thiopyran-4-yl))amino)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(methyl(2-(methylsulfonyl)ethyl)amino)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

N-(7-((2-(N-acetylsulfamoyl)ethyl)(methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yl)-4-tert-butylbenzamide;

4-tert-butyl-N-(7-(methyl(2-(methylsulfonamido)ethyl)amino)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide;

4-tert-butyl-N-(7-(2-(methylsulfonyl)ethoxy)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide; and

a pharmaceutically acceptable salt of any one of the aforementioned compounds.