Patent ID: 8420819

Claim:
A process for crystallizing a compound of Formula (I) wherein: R 1 is an aryl or heteroaryl group, each optionally independently substituted with one, two, or three substituent groups selected from C 1 -C 5 alkyl, aminocarbonyl, C 1 -C 5 alkylaminocarbonyl, C 1 -C 5 dialkylaminocarbonyl, aminosulfonyl, C 1 -C 5 alkylaminosulfonyl, C 1 -C 5 dialkylaminosulfonyl, halogen, hydroxyl, cyano, and C 1 -C 5 alkylthio wherein the sulfur atom is optionally oxidized to a sulfoxide or sulfone; R 2 is C 1 -C 5 alkylthio wherein the sulfur atom is optionally oxidized to a sulfoxide or sulfone, optionally independently substituted with one, two, or three substituent groups selected from halogen, hydroxy, oxo, cyano, alkoxyalkyl, and aminocarbonyl; X is CH or N; and Y is CH or N, wherein X and Y are not both CH, or a tautomer, optical isomer, co-crystal, or salt thereof, the process comprising: (a) dissolving the free base of the compound of Formula (I) in a primary organic solvent to obtain a first solution; (b) adding an acid to the first solution to obtain a second solution; (c) combining an organic antisolvent with the second solution to obtain a third solution, wherein the antisolvent is miscible with the primary organic solvent and in which the compound of Formula (I) has a lesser solubility than in the primary organic solvent; (d) achieving supersaturation of the compound of Formula (I) in the third solution to obtain a supersaturated fourth solution; and (e) obtaining crystals of the compound of Formula (I) or a tautomer, optical isomer, co-crystal, or salt thereof.