In a 25 mL sealable tube under nitrogen were combined 1-(1-methylethyl)-6-phenyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (70 mg, 0.25 mmol) and 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone.HCl (56.3 mg, 0.3 mmol) in DMSO (3 mL). 1-hydroxy-7-azabenzotriazole (51 mg, 0.37 mmol) was added and the resulting mixture was degassed with nitrogen for 10 min. N-methylmorpholine (0.1 ml, 0.87 mmol) and EDC (72 mg, 0.37 mmol) were added, the vessel was sealed, and the bright yellow mixture was stirred at room temperature for 2 days. Next added 2 mL of water, and the contents were stirred for 10 min. Solids that precipitated were sonicated, and allowed to stand at room temperature for 10 min. The reaction contents were filtered and washed with water. The solid was treated with 2 mL of EtOH, sonicated and heated, and then allowed to cool to room temperature. The contents were filtered, washed with water and dried to afford the title compound (74 mg, 70%) as a white solid. LCMS E-S (M+H)=416.3. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.58 (s, 1H), 8.98 (t, J=4.80 Hz, 1H), 8.38 (s, 1H), 8.25-8.30 (m, 2H), 8.17 (s, 1H), 7.49-7.59 (m, 3H), 5.91 (s, 1H), 5.30-5.38 (m, 1H), 4.42 (d, J=4.80 Hz, 2H), 2.23 (s, 3H), 2.13 (s, 3H), 1.55 (d, J=6.57 Hz, 6H).
