Imidazolepyridine compounds and uses thereof

1. A compound of Formula (IA):

or a pharmaceutically acceptable salt thereof, wherein:

A is

R 1 and R 2 are each independently H or halogen;

R 3 is selected from: halogen, phenyl, and a 5- to 6-membered heteroaryl containing carbon atoms and 1-4 heteroatoms selected from N, NR a , O, and S(O) p ; wherein said phenyl and heteroaryl are substituted with 0-3 R 3A ;

each R 3A is independently selected from: halogen, CN, OH, —(O) m —(C 1 -C 6 alkyl substituted with 0-1 R 3B ), C 1 -C 6 haloalkyl, C 1 -C 6 haloalkoxy, R 3C , —OR 3C , —C(═O)R 3D , NR 3E R 3F , —C(═O)NR 3E R 3F , —NHC(═O)R 3D , —S(═O) 2 R 3D , —S(═O) 2 NR 3E R 3F , —NHS(═O) 2 (C 1 -C 4 alkyl), and —CR 3C R 3E R 3G ;

R 3B is selected from: OH, NR e R f , C 1 -C 4 alkoxy, —C(═O)NR e R f , —S(═O) 2 (C 1 -C 4 alkyl), —NHC(═O)(C 1 -C 4 alkyl), and a 5- to 6-membered heterocycloalkyl containing carbon atoms and 1-2 heteroatoms selected from N, NR a , O, and S(O) p ; wherein said heterocycloalkyl is substituted with 0-2 R c ;

each R 3C is independently selected from: C 3 -C 6 cycloalkyl, phenyl, and a 4- to 7-membered heterocycle containing carbon atoms and 1-4 heteroatoms selected from N, NR a , O, and S(O) p ; wherein each moiety is substituted with 0-2 R c ;

each R 3D is independently selected from: C 1 -C 4 alkyl and R 3C ;

R 3E and R 3G are, at each occurrence, independently selected from: H and C 1 -C 4 alkyl;

each R 3F is independently selected from: H and C 1 -C 4 alkyl substituted with 0-1 R d ;

R 4 is H, halogen or C 1 -C 4 alkyl;

R 5 is OH or C 1 -C 4 alkyl;

R 6 is selected from: H, halogen, CN, C 2 -C 4 alkynyl, —CO(C 1 -C 4 alkyl), —CO 2 H, —CO 2 (C 1 -C 4 alkyl), C 1 -C 4 alkyl substituted with 0-1 R b , —C(═O)NR 3E R 3D , —S(═O)R 3D , —S(═O) 2 R 3D , —S(═O) 2 NR 3E R 3F , —CONHNH 2 , phenyl substituted with 0-2 R b , a 5- to 6-membered heteroaryl containing carbon atoms and 1-4 heteroatoms selected from N, NR a , O, and S(O) p ; wherein said heteroaryl is substituted with 0-3 R 3A ;

R 7 is H;

R 11 is H, halogen, or NH 2 ;

R 12 is H, OCH 3 , or halogen;

R 13 is H or halogen;

R 14 is H, halogen, CH 3 , or OCH 3 ;

R 15 is H, halogen, CH 3 , OH, OCH 3 , OCH 2 F, OCHF 2 , or OCF 3 ;

each R a is independently selected from: H, C 1 -C 4 alkyl substituted with 0-1 R b , —C(═O)H, —C(═O)(C 1 -C 4 alkyl), —CO 2 (C 1 -C 4 alkyl), C 3 -C 6 cycloalkyl, and benzyl;

R b is selected from: halogen, OH and C 1 -C 4 alkoxy;

each R c is independently selected from: ═O, halogen, OH, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, and C 1 -C 4 haloalkoxy;

R d is selected from: OH and NR e R f ;

R e and R f are, at each occurrence, independently selected from: H and C 1 -C 4 alkyl;

each p is independently selected from 0, 1 and 2; and

m and n are, at each occurrence, independently selected from 0 and 1.

2. The compound or a pharmaceutically acceptable salt thereof, according to claim 1 , wherein:

each R 3A is independently selected from: halogen, CN, —(O) m —(C 1 -C 4 alkyl substituted with 0-1 R 3B ), C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, R 3C , —C(═O)R 3D , NR 3E R 3F , —C(═O)NR 3E R 3F , —S(═O) 2 R 3D , —S(═O) 2 NR 3E R 3F , —NHS(═O) 2 (C 1 -C 4 alkyl), and —O—C 3 -C 6 cycloalkyl;

R 6 is selected from: H, halogen, CN, C 2 -C 4 alkynyl, —CO(C 1 -C 4 alkyl), —CO 2 H, —CO 2 (C 1 -C 4 alkyl), C 1 -C 4 alkyl substituted with 0-1 R b , —C(═O)NR 3E R 3D , —S(═O)R 3D , —S(═O) 2 R 3D , —S(═O) 2 NR 3E R 3F , —CONHNH 2 , phenyl substituted with 0-1 R b , oxazolyl, tetrazolyl, pyridyl substituted with 0-2 R b ;

each R a is independently selected from: H, C 1 -C 4 alkyl substituted with 0-1 R b , —C(═O)H, —C(═O)(C 1 -C 4 alkyl), —CO 2 (C 1 -C 4 alkyl), and C 3 -C 6 cycloalkyl;

and

R 4 is H.

3. The compound or a pharmaceutically acceptable salt thereof, according to claim 1 , wherein:

R 1 is H or F;

R 2 is H; and

R 3 is selected from: phenyl, and a 5- to 6-membered heteroaryl containing carbon atoms and 1-2 heteroatoms selected from O, N and NR a ; wherein said phenyl and heteroaryl are substituted with 0-3 R 3A ;

m is independently selected from 0 and 1; and

n is 0.

4. The compound or a pharmaceutically acceptable salt thereof, according to claim 1 , wherein:

A is

R 1 is H or F;

R 3 is selected from: phenyl substituted with 0-3 R 3A , pyridyl substituted with 0-2 R 3A , pyrimidinyl substituted with 0-2 R 3A , isoxazolyl substituted with 0-2 R 3A , and

each R 3A is independently selected from: halogen, CN, C 1 -C 4 alkyl substituted with 0-1 R 3B , C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl substituted with 0-1 R 3B , NH(C 1 -C 4 alkyl substituted with 0-1 OH), N(C 1 -C 4 alkyl) 2 , —C(═O)N(C 1 -C 4 alkyl) 2 , —S(═O) 2 (C 1 -C 4 alkyl), —S(═O) 2 NH 2 ,

—S(═O) 2 N(C 1 -C 4 alkyl) 2 , —NHS(═O) 2 (C 1 -C 4 alkyl),

R 3B is selected from: halogen, OH, N(C 1 -C 4 alkyl) 2

R 4 is H;

R 6 is selected from: H, halogen, CN, C 2 -C 4 alkynyl, —CO(C 1 -C 4 alkyl), —CO 2 H, —CO 2 (C 1 -C 4 alkyl), C 1 -C 4 alkyl substituted with 0-1 OH, —CONH(C 1 -C 4 alkyl substituted with 0-1 OH), —C(═O)N(C 1 -C 4 alkyl) 2 , —S(═O) 2 (C 1 -C 4 alkyl), —S(═O)Ph, —S(═O) 2 Ph, —CONHNH 2 , phenyl substituted with 0-1 C 1 -C 4 alkoxy, oxazolyl, tetrazolyl, pyridyl substituted with 0-2 C 1 -C 4 alkyl,

R 7 is H; and

each R a is independently selected from: H, C 1 -C 4 alkyl substituted with 0-1 OH, —CO(C 1 -C 4 alkyl), and cyclopropyl.

5. The compound or a pharmaceutically acceptable salt thereof, according to claim 1 , wherein:

R 3 is selected from: phenyl substituted with 0-3 R 3A , pyridyl substituted with 0-2 R 3A , and pyrimidinyl substituted with 0-2 R 3A ;

each R 3A is independently selected from: F, Cl, CH 3 , —CH 2 OH, CH 2 F, CHF 2 , CF 3 , CN, —OCH 3 , —OCH 2 CH 3 , —OCH(CH 3 ) 2 , —OCHF 2 , —C(═O)N(CH 3 ) 2 , —CH 2 NHC(═O)CH 3 , —S(═O) 2 CH 3 , NH 2 , cyclopropyl,

and

R 6 is selected from: H, Cl, CN, —C(═O)N(C 1 -C 4 alkyl) 2 , and —S(═O) 2 (C 1 -C 4 alkyl).

6. The compound or a pharmaceutically acceptable salt thereof, according to claim 1 , wherein:

R 1 is F.

7. The compound or a pharmaceutically acceptable salt thereof, according to claim 1 , wherein said compound is selected from

8-(2,4-dimethylpyrimidin-5-yl)-N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)imidazo[1,5-c]pyrimidin-5-amine;

5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)-N-methyl-8-(2-methylpyridin-3-yl)imidazo[1,5-c]pyrimidine-1-carboxamide;

8-(2,4-dimethylpyrimidin-5-yl)-5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)imidazo[1,5-c]pyrimidine-1-carbonitrile;

N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)-1-methyl-8-(4-(methylsulfonyl)phenyl)imidazo[1,5-c]pyrimidin-5-amine;

8-(1,3-dimethyl-1H-pyrazol-5-yl)-5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)imidazo[1,5-c]pyrimidine-1-carbonitrile;

5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)-8-(4-methyl-1H-imidazol-1-yl)imidazo[1,5-c]pyrimidine-1-carbonitrile;

(8-(2,4-dimethylpyrimidin-5-yl)-5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)imidazo[1,5-c]pyrimidin-1-yl)methanol;

1-chloro-8-(2,4-dimethylpyrimidin-5-yl)-N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)imidazo[1,5-c]pyrimidin-5-amine;

N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)-8-(2-methylpyridin-3-yl)-1-(methylsulfonyl)imidazo[1,5-c]pyrimidin-5-amine;

8-(2,4-dimethylpyrimidin-5-yl)-N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)-1-(oxazol-2-yl)imidazo[1,5-c]pyrimidin-5-amine;

1-ethynyl-N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)-8-(2-methylpyridin-3-yl)imidazo[1,5-c]pyrimidin-5-amine;

8-(2-(difluoromethyl)pyridin-3-yl)-N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)-1-(methylsulfonyl)imidazo[1,5-c]pyrimidin-5-amine;

8-(2,4-dimethylpyrimidin-5-yl)-N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)-1-(phenylsulfinyl)imidazo[1,5-c]pyrimidin-5-amine;

8-(2,4-dimethylpyrimidin-5-yl)-N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)-1-(phenylsulfonyl)imidazo[1,5-c]pyrimidin-5-amine;

1-(8-(2,4-dimethylpyrimidin-5-yl)-5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)imidazo[1,5-c]pyrimidin-1-yl)ethan-1-one;

8-(4-((dimethylamino)methyl)phenyl)-N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)imidazo[1,5-c]pyrimidin-5-amine;

4-(5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)imidazo[1,5-c]pyrimidin-8-yl)-N,N-dimethylbenzenesulfonamide;

N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)-8-(4-(methylsulfonyl)phenyl)imidazo[1,5-c]pyrimidin-5-amine;

N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)-8-(pyridin-4-yl)imidazo[1,5-c]pyrimidin-5-amine;

N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)-8-(2-fluoropyridin-3-yl)imidazo[1,5-c]pyrimidin-5-amine;

N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)-8-(6-(methylsulfonyl)pyridin-3-yl)imidazo[1,5-c]pyrimidin-5-amine;

4-(5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)imidazo[1,5-c]pyrimidin-8-yl)benzenesulfonamide;

N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)-8-(2-methylpyridin-4-yl)imidazo[1,5-c]pyrimidin-5-amine;

N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)-8-(2-methylpyridin-3-yl)imidazo[1,5-c]pyrimidin-5-amine;

N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)-8-(2-methyl-1,2,3,4-tetrahydroisoquinolin-7-yl)imidazo[1,5-c]pyrimidin-5-amine;

N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)-8-(3-(methylsulfonyl)phenyl)imidazo[1,5-c]pyrimidin-5-amine;

N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)-8-(pyridin-3-yl)imidazo[1,5-c]pyrimidin-5-amine;

N-(4-(5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)imidazo[1,5-c]pyrimidin-8-yl)phenyl)methanesulfonamide;

N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)-8-(4-(isopropylsulfonyl)phenyl)imidazo[1,5-c]pyrimidin-5-amine;

5-(5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)imidazo[1,5-c]pyrimidin-8-yl)picolinonitrile;

8-(6-(2-(dimethylamino)ethyl)pyridin-3-yl)-N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)imidazo[1,5-c]pyrimidin-5-amine;

N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)-8-(1-methyl-1H-pyrazol-5-yl)imidazo[1,5-c]pyrimidin-5-amine;

2-(5-(5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)imidazo[1,5-c]pyrimidin-8-yl)pyridin-2-yl)ethan-1-ol;

N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)-8-(2-fluoropyridin-4-yl)imidazo[1,5-c]pyrimidin-5-amine;

N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)-8-(3-methylpyridin-4-yl)imidazo[1,5-c]pyrimidin-5-amine;

(4-(5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)imidazo[1,5-c]pyrimidin-8-yl)phenyl)(pyrrolidin-1-yl)methanone;

N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)-8-(2-methyl-6-(methylsulfonyl)pyridin-3-yl)imidazo[1,5-c]pyrimidin-5-amine;

N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)-8-(4-(pyrrolidin-1-ylmethyl)phenyl)imidazo[1,5-c]pyrimidin-5-amine;

N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)-8-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)imidazo[1,5-c]pyrimidin-5-amine;

8-(6-(dimethylamino)pyridin-3-yl)-N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)imidazo[1,5-c]pyrimidin-5-amine;

N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)-8-(2-methyl-4-(methylsulfonyl)phenyl)imidazo[1,5-c]pyrimidin-5-amine;

8-(2,6-dimethylpyridin-3-yl)-N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)imidazo[1,5-c]pyrimidin-5-amine;

2-((5-(5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)imidazo[1,5-c]pyrimidin-8-yl)pyrimidin-2-yl)amino)ethan-1-ol;

8-(1,3-dimethyl-1H-pyrazol-5-yl)-N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)imidazo[1,5-c]pyrimidin-5-amine;

N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)-8-(1,3,5-trimethyl-1H-pyrazol-4-yl)imidazo[1,5-c]pyrimidin-5-amine;

N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)-8-(4-methylpyrimidin-5-yl)imidazo[1,5-c]pyrimidin-5-amine;

N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)-8-(3-methyl-4-(methylsulfonyl)phenyl)imidazo[1,5-c]pyrimidin-5-amine;

2-(4-(5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)imidazo[1,5-c]pyrimidin-8-yl)-3,5-dimethyl-1H-pyrazol-1-yl)ethan-1-ol;

N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)-8-(2-methylpyrimidin-5-yl)imidazo[1,5-c]pyrimidin-5-amine;

8-(2-(difluoromethyl)pyridin-3-yl)-N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)imidazo[1,5-c]pyrimidin-5-amine;

8-(4-(difluoromethyl)pyridin-3-yl)-N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)imidazo[1,5-c]pyrimidin-5-amine;

N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)-8-(1-isopropyl-3-methyl-1H-pyrazol-4-yl)imidazo[1,5-c]pyrimidin-5-amine;

5-(5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)imidazo[1,5-c]pyrimidin-8-yl)-N,N,4-trimethylpicolinamide;

8-(4-(azetidin-1-ylmethyl)phenyl)-N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)imidazo[1,5-c]pyrimidin-5-amine;

2,2-difluoro-2-(5-(5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)imidazo[1,5-c]pyrimidin-8-yl)-6-methylpyridin-2-yl)ethan-1-ol;

8-(6-(difluoromethyl)-2-methylpyridin-3-yl)-N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)imidazo[1,5-c]pyrimidin-5-amine;

N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)-8-(2-(fluoromethyl)-3-methylpyridin-4-yl)imidazo[1,5-c]pyrimidin-5-amine;

8-(6-(1,1-difluoro-2-(pyrrolidin-1-yl)ethyl)-2-methylpyridin-3-yl)-N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)imidazo[1,5-c]pyrimidin-5-amine;

8-(6-(difluoromethyl)pyridin-3-yl)-N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)imidazo[1,5-c]pyrimidin-5-amine;

N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)-8-(2-isopropoxy-4-methylpyrimidin-5-yl)imidazo[1,5-c]pyrimidin-5-amine;

N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)-8-(4-methyl-1H-imidazol-1-yl)imidazo[1,5-c]pyrimidin-5-amine;

5-(5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)imidazo[1,5-c]pyrimidin-8-yl)-N,N,6-trimethylpicolinamide;

N-(benzofuran-4-ylmethyl)-8-(4-((dimethylamino)methyl)phenyl)imidazo[1,5-c]pyrimidin-5-amine;

N-(benzofuran-4-ylmethyl)-8-(pyridin-4-yl)imidazo[1,5-c]pyrimidin-5-amine;

N-(benzofuran-4-ylmethyl)-8-(6-(piperazin-1-yl)pyridin-3-yl)imidazo[1,5-c]pyrimidin-5-amine;

8-(4-((dimethylamino)methyl)phenyl)-N-((5-fluorobenzofuran-4-yl)methyl)imidazo[1,5-c]pyrimidin-5-amine;

5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)-8-(2-methylpyridin-3-yl)imidazo[1,5-c]pyrimidine-1-carbonitrile;

8-bromo-5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)imidazo[1,5-c]pyrimidine-1-carbonitrile;

5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)-8-(4-(pyrrolidin-1-ylmethyl)phenyl)imidazo[1,5-c]pyrimidine-1-carbonitrile;

5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)-8-(6-methylpyridin-3-yl)imidazo[1,5-c]pyrimidine-1-carbonitrile;

8-(2-(difluoromethyl)pyridin-3-yl)-5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)imidazo[1,5-c]pyrimidine-1-carbonitrile;

5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)-8-(pyridin-3-yl)imidazo[1,5-c]pyrimidine-1-carbonitrile;

8-(2,6-dimethylpyridin-3-yl)-5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)imidazo[1,5-c]pyrimidine-1-carbonitrile;

5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)-8-(4-(1-(pyrrolidin-1-yl)ethyl)phenyl)imidazo[1,5-c]pyrimidine-1-carbonitrile;

5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)-8-(6-methoxy-4-methylpyridin-3-yl)imidazo[1,5-c]pyrimidine-1-carbonitrile;

5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)-8-(2-(hydroxymethyl)pyridin-3-yl)imidazo[1,5-c]pyrimidine-1-carbonitrile;

5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)-8-(6-(methylsulfonyl)pyridin-3-yl)imidazo[1,5-c]pyrimidine-1-carbonitrile;

5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)-8-(2-(1-hydroxypropyl)-4-methylpyrimidin-5-yl)imidazo[1,5-c]pyrimidine-1-carbonitrile;

8-(6-(4-ethylpiperazin-1-yl)pyridin-3-yl)-5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)imidazo[1,5-c]pyrimidine-1-carbonitrile;

5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)-8-(6-morpholinopyridin-3-yl)imidazo[1,5-c]pyrimidine-1-carbonitrile;

8-(2-(3,5-dimethylpiperazin-1-yl)-4-methylpyrimidin-5-yl)-5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)imidazo[1,5-c]pyrimidine-1-carbonitrile;

5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)-8-(4-methyl-2-morpholinopyrimidin-5-yl)imidazo[1,5-c]pyrimidine-1-carbonitrile;

5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)-8-(1-methyl-1H-imidazol-5-yl)imidazo[1,5-c]pyrimidine-1-carbonitrile;

5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)-8-(6-(piperazin-1-yl)pyridin-3-yl)imidazo[1,5-c]pyrimidine-1-carbonitrile;

8-(6-(4-acetylpiperazin-1-yl)pyridin-3-yl)-5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)imidazo[1,5-c]pyrimidine-1-carbonitrile;

5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)-8-(1-(2-hydroxyethyl)-3,5-dimethyl-1H-pyrazol-4-yl)imidazo[1,5-c]pyrimidine-1-carbonitrile;

ethyl 8-bromo-5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)imidazo[1,5-c]pyrimidine-1-carboxylate;

ethyl 5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)-8-(4-(methylsulfonyl)phenyl)imidazo[1,5-c]pyrimidine-1-carboxylate;

ethyl 8-(2,6-dimethylpyridin-3-yl)-5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)imidazo[1,5-c]pyrimidine-1-carboxylate;

ethyl 8-(2,4-dimethylpyrimidin-5-yl)-5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)imidazo[1,5-c]pyrimidine-1-carboxylate;

ethyl 5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)-8-(2-methylpyridin-3-yl)imidazo[1,5-c]pyrimidine-1-carboxylate;

N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)-1-(methylsulfonyl)-8-(4-(methylsulfonyl)phenyl)imidazo[1,5-c]pyrimidin-5-amine;

8-(2,4-dimethylpyrimidin-5-yl)-N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)-1-(methylsulfonyl)imidazo[1,5-c]pyrimidin-5-amine;

N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)-1-(methylsulfonyl)-8-(pyridin-3-yl)imidazo[1,5-c]pyrimidin-5-amine;

8-bromo-N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)-1-(methylsulfonyl)imidazo[1,5-c]pyrimidin-5-amine;

8-(2,4-dimethylpyrimidin-5-yl)-1-(ethylsulfonyl)-N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)imidazo[1,5-c]pyrimidin-5-amine;

5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)-N,N-dimethyl-8-(2-methylpyridin-3-yl)imidazo[1,5-c]pyrimidine-1-carboxamide;

5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)-8-(2-methylpyridin-3-yl)-N-(oxetan-3-yl)imidazo[1,5-c]pyrimidine-1-carboxamide;

5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)-N-(2-hydroxyethyl)-8-(2-methylpyridin-3-yl)imidazo[1,5-c]pyrimidine-1-carboxamide;

5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)-8-(2-methylpyridin-3-yl)imidazo[1,5-c]pyrimidine-1-carbohydrazide;

1-chloro-N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)-8-(4-(methylsulfonyl)phenyl)imidazo[1,5-c]pyrimidin-5-amine;

N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)-8-(4-(methylsulfonyl)phenyl)-1-phenylimidazo[1,5-c]pyrimidin-5-amine;

N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)-8-(2-methylpyridin-3-yl)-1-phenylimidazo[1,5-c]pyrimidin-5-amine;

N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)-1-(2-methylpyridin-3-yl)-8-(4-(methylsulfonyl)phenyl)imidazo[1,5-c]pyrimidin-5-amine;

1-(2,6-dimethylpyridin-3-yl)-8-(2,4-dimethylpyrimidin-5-yl)-N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)imidazo[1,5-c]pyrimidin-5-amine;

8-(2,4-dimethylpyrimidin-5-yl)-N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)-1-(6-methylpyridin-3-yl)imidazo[1,5-c]pyrimidin-5-amine;

N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)-8-(2-methylpyridin-3-yl)-1-(6-methylpyridin-3-yl)imidazo[1,5-c]pyrimidin-5-amine;

N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)-8-(2-methylpyridin-3-yl)-1-((trimethylsilyl)ethynyl)imidazo[1,5-c]pyrimidin-5-amine;

N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)-1-(4-isopropoxyphenyl)-8-(4-(methylsulfonyl)phenyl)imidazo[1,5-c]pyrimidin-5-amine;

N-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)-8-(4-(methylsulfonyl)phenyl)-1-(oxazol-2-yl)imidazo[1,5-c]pyrimidin-5-amine;

5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)-8-(1H-imidazol-1-yl)imidazo[1,5-c]pyrimidine-1-carbonitrile; and

(5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)-8-(2-methylpyridin-3-yl)imidazo[1,5-c]pyrimidin-1-yl)methanol.

8. A pharmaceutical composition, comprising one or more pharmaceutically acceptable carriers and a compound of claim 1 .

9. The pharmaceutical composition of claim 8 further comprising at least one additional therapeutic agent.

10. The pharmaceutical composition of claim 9 said at least one additional therapeutic agent is selected from an anti-cancer agent, an immunomodulator, an anti-allergic agent, an anti-emetic, a pain reliever and a cytoprotective agent.