To a solution of 1-[3-(3-bromo-5-chlorophenoxy)-4-methylpyridin-2-yl]methanamine (125 mg, 0.382 mmol), 1H-pyrazolo[3,4-b]pyridin-3-ylacetic acid compound with ammonium chloride (1:1), (102 mg, 0.443 mmol), HOAT (5.2 mg, 0.038 mmol) and TEA (53 μL, 0.382 mmol) in DMF (2 mL) was added EDC (80 mg, 0.42 mmol), and the mixture was stirred for 2.2 hours. The mixture was then filtered and purified using Waters PrepPak column and eluting with a gradient of 5-95% ACN/H2O with 0.1% TFA. The desired fractions were lyophilized to give title compound.
