Solid forms of an HPK1 inhibitor

1. A unit dosage form comprising a solid form of Compound 1 having the formula:

wherein the solid form has crystalline Form I, and wherein the solid form has at least one characteristic X-ray powder diffraction (“XRPD”) peak selected from about 6.7, about 9.9, about 13.4, about 14.1, about 15.5, about 18.3, about 19.9, and about 20.4 degrees 2-theta.

2. The unit dosage form of claim 1 , wherein the solid form has at least one characteristic XRPD peak selected from about 6.7, about 9.9, about 13.4, and about 15.5 degrees 2-theta.

3. The unit dosage form of claim 1 , wherein the solid form has an XRPD pattern with characteristic peaks as substantially shown in FIG. 1 .

4. The unit dosage form of claim 1 , wherein the solid form exhibits a DSC thermogram having endotherm peaks at temperatures of about 86° C. and about 183° C.

5. The unit dosage form of claim 1 , wherein the solid form has a DSC thermogram substantially as depicted in FIG. 2 .

6. The unit dosage form of claim 1 , wherein the solid form has a TGA thermogram substantially as depicted in FIG. 3 .

7. A unit dosage form comprising a salt which is an acid salt of N-(2-((2S,4S)-4-Amino-2-(hydroxymethyl)pyrrolidin-1-yl)-5-fluorophenyl)-2-(2-fluoro-6-methoxyphenyl)pyrimidine-4-carboxamide, having the structure:

wherein the acid is selected from phosphoric acid, hydrochloric acid, L-(+)-tartaric acid, malic acid, camphorsulfonic acid, mandelic acid, and citric acid, wherein the salt is crystalline, and wherein:

the phosphoric acid salt of Compound 1 has at least one characteristic XRPD peak selected from about 6.3, about 6.4, about 7.0, about 8.9, about 11.2, about 12.5, about 19.9, and about 22.9 degrees 2-theta;

the hydrochloric acid salt of Compound 1 has at least one characteristic XRPD peak selected from about 6.7, about 9.1, about 11.0, about 12.7, about 13.5, about 15.5, about 17.1, and about 23.4 degrees 2-theta;

the L-(+)-tartaric acid salt of Compound 1 has at least one characteristic XRPD peak selected from about 4.9, about 7.9, about 9.8, about 15.9, about 16.9, about 19.6, and about 23.0 degrees 2-theta;

the malic acid salt of Compound 1 has at least one characteristic XRPD peak selected from about 5.2, about 7.9, about 10.4, about 14.3, about 15.8, about 16.6, about 18.0, about 21.0, and about 21.2 degrees 2-theta;

the camphorsulfonic acid salt of Compound 1 has at least one characteristic XRPD peak selected from about 4.9, about 5.9, about 10.9, about 14.4, about 15.0, about 15.1, about 19.8, about 20.1, and about 25.8 degrees 2-theta;

the mandelic acid salt of Compound 1 has at least one characteristic XRPD peak selected from about 4.2, about 5.0, about 5.4, about 5.8, about 6.9, about 14.2, about 15.3, about 19.0, and about 19.6 degrees 2-theta; and

the citric acid salt of Compound 1 has at least one characteristic XRPD peak selected from about 7.3, about 9.0, about 13.6, about 16.6, about 18.1, about 18.3, about 19.5, about 20.1, and about 20.9 degrees 2-theta.

8. The unit dosage form of claim 7 , wherein the salt is N-(2-((2S,4S)-4-Amino-2-(hydroxymethyl)pyrrolidin-1-yl)-5-fluorophenyl)-2-(2-fluoro-6-methoxyphenyl)pyrimidine-4-carboxamide phosphate.

9. The unit dosage form of claim 7 , wherein the salt is N-(2-((2S,4S)-4-Amino-2-(hydroxymethyl)pyrrolidin-1-yl)-5-fluorophenyl)-2-(2-fluoro-6-methoxyphenyl)pyrimidine-4-carboxamide hydrochloride.

10. The unit dosage form of claim 7 , wherein the salt is N-(2-((2S,4S)-4-Amino-2-(hydroxymethyl)pyrrolidin-1-yl)-5-fluorophenyl)-2-(2-fluoro-6-methoxyphenyl)pyrimidine-4-carboxamide L-tartrate.

11. The unit dosage form of claim 7 , wherein the salt is N-(2-((2S,4S)-4-Amino-2-(hydroxymethyl)pyrrolidin-1-yl)-5-fluorophenyl)-2-(2-fluoro-6-methoxyphenyl)pyrimidine-4-carboxamide malate.

12. The unit dosage form of claim 7 , wherein the salt is N-(2-((2S,4S)-4-Amino-2-(hydroxymethyl)pyrrolidin-1-yl)-5-fluorophenyl)-2-(2-fluoro-6-methoxyphenyl)pyrimidine-4-carboxamide camsylate.

13. The unit dosage form of claim 7 , wherein the salt is N-(2-((2S,4S)-4-Amino-2-(hydroxymethyl)pyrrolidin-1-yl)-5-fluorophenyl)-2-(2-fluoro-6-methoxyphenyl)pyrimidine-4-carboxamide mandelate.

14. The unit dosage form of claim 7 , wherein the salt is N-(2-((2S,4S)-4-Amino-2-(hydroxymethyl)pyrrolidin-1-yl)-5-fluorophenyl)-2-(2-fluoro-6-methoxyphenyl)pyrimidine-4-carboxamide citrate.

15. The unit dosage form of claim 8 , wherein the salt has an X-ray powder diffraction pattern with characteristic peaks as substantially shown in FIG. 4 .

16. The unit dosage form of claim 9 , wherein the salt has an X-ray powder diffraction pattern with characteristic peaks as substantially shown in FIG. 7 .

17. The unit dosage form of claim 10 , wherein the salt has an X-ray powder diffraction pattern with characteristic peaks as substantially shown in FIG. 10 .

18. The unit dosage form of claim 11 , wherein the salt has an X-ray powder diffraction pattern with characteristic peaks as substantially shown in FIG. 13 .

19. The unit dosage form of claim 12 , wherein the salt has an X-ray powder diffraction pattern with characteristic peaks as substantially shown in FIG. 16 .

20. The unit dosage form of claim 13 , wherein the salt has an X-ray powder diffraction pattern with characteristic peaks as substantially shown in FIG. 19 .

21. The unit dosage form of claim 14 , wherein the salt has an X-ray powder diffraction pattern with characteristic peaks as substantially shown in FIG. 22 .

22. A unit dosage form comprising a salt which is an acid salt of N-(2-((2S,4S)-4-Amino-2-(hydroxymethyl)pyrrolidin-1-yl)-4-(4-cyanopyridin-3-yl)phenyl)-2-(2-fluoro-6-methoxyphenyl)pyrimidine-4-carboxamide, having the structure:

wherein the acid is selected from phosphoric acid and hydrochloric acid, wherein the salt is crystalline, and wherein:

the phosphoric acid salt of Compound 2 has at least one characteristic XRPD peak selected from about 5.9, about 6.7, about 10.2, about 13.4, about 14.5, about 15.5, about 16.5, about 17.4, and about 18.0 degrees 2-theta; and

the hydrochloric acid salt of Compound 2 has at least one characteristic XRPD peak selected from about 6.2, about 6.8, about 11.2, about 12.5, about 13.6, about 17.3, about 18.4, about 21.6, and about 22.3 degrees 2-theta.

23. The unit dosage form of claim 22 , wherein the salt is N-(2-((2S,4S)-4-Amino-2-(hydroxymethyl)pyrrolidin-1-yl)-4-(4-cyanopyridin-3-yl)phenyl)-2-(2-fluoro-6-methoxyphenyl)pyrimidine-4-carboxamide phosphate.

24. The unit dosage form of claim 22 , wherein the salt is N-(2-((2S,4S)-4-Amino-2-(hydroxymethyl)pyrrolidin-1-yl)-4-(4-cyanopyridin-3-yl)phenyl)-2-(2-fluoro-6-methoxyphenyl)pyrimidine-4-carboxamide hydrochloride.

25. The unit dosage form of claim 23 , wherein the salt has an X-ray powder diffraction pattern with characteristic peaks as substantially shown in FIG. 25 .

26. The unit dosage form of claim 24 , wherein the salt has an X-ray powder diffraction pattern with characteristic peaks as substantially shown in FIG. 28 .