6-Cyclopropyl-3-methyl-1-(1-methyl-4-piperidinyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (150 mg, 0.477 mmol), 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone (117 mg, 0.620 mmol), 1-hydroxy-7-azabenzotriazole (130 mg, 0.954 mmol), EDC (183 mg, 0.954 mmol) and N-methylmorpholine (0.210 mL, 1.909 mmol) were suspended in DMSO (10 mL) and stirred at room temperature for 16 h. Next was added 25 mL of water, stirred for 10 minutes, and then extracted with EtOAc (5×). The organic layers were concentrated in vacuo to afford 20 mg product. The aqueous phase was concentrated in vacuo and the crude residue purified by reverse phase HPLC (mobile phase: 10-60% ACN in H2O, 0.1% NH4OH) to afford additional product. The final product was collected as a solid, 0.100 g (47%). LCMS E-S (M+H)=449.0. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.97-1.05 (m, 4H), 1.79 (d, J=9.60 Hz, 2H), 2.11 (s, 3H), 2.15 (d, J=8.34 Hz, 3H), 2.21 (s, 3H), 2.23-2.27 (m, 3H), 2.35 (s, 3H), 2.91 (d, J=8.08 Hz, 2H), 4.33 (d, J=4.80 Hz, 2H), 4.49-4.72 (m, 1H), 5.86 (s, 1H), 6.97 (s, 1H), 6.92-7.07 (m, 1H), 8.58 (t, J=4.93 Hz, 1H), 11.50 (s, 1H).
