Benzoic Acid → 3-(4-(aminomethyl)-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamido)phenyl dimethylcarbamate benzoate

A reactor was charged with 3-(4-(aminomethyl)-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamido)phenyl dimethylcarbamate freebase (101.1 mg, 0.224 mmol, 1 eq) and MeOH (1 mL). To the clear solution was added benzoic acid (33.9 mg, 0.278 mmol, 1.24 eq) and the resulting mixture was stirred at room temperature for 5 min to give a slurry. Acetonitrile (2 mL) was added and the slurry was heated to 70-73° C. and stirred for 5 minutes to give a solution. After being cooled to room temperature, the reaction mixture was stirred for 2 hours. The precipitate was collected by filtration and the cake was washed with MTBE (1 mL) and dried at 40-45° C. under vacuum overnight to provide the 3-(4-(aminomethyl)-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamido)phenyl dimethylcarbamate benzoate (94.8 mg, 75%) as an off-white solid