1,2-Dichloroethane → 1-(1,1-Dimethylethyl)-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-3-methyl-6-[4-(methyloxy)phenyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

Participants

Reaction Steps

To a solution of 1-(1,1-dimethylethyl)-3-methyl-6-[4-(methyloxy)phenyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (70 mg, 0.206 mmol) in DMSO (1 mL) were added 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone (19.10 mg, 0.101 mmol), N-methylmorpholine (0.030 mL, 0.270 mmol), 1-hydroxy-7-azabenzotriazole (18.37 mg, 0.135 mmol) and EDC (25.9 mg, 0.135 mmol), and the mixture was stirred overnight at room temperature. The reaction mixture was quenched with water (10 mL), stirred for 10 min., and filtered. The contents were dried under high vacuum and collected as 71 mg (71%). LCMS E-S (M+H)=474.1. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.79 (s, 9H), 2.12 (s, 3H), 2.25 (s, 3H), 2.39 (s, 3H), 3.33 (s, 1H), 4.38 (d, J=4.80 Hz, 2H), 5.88 (s, 1H), 7.10 (d, J=8.84 Hz, 2H), 7.61 (s, 1H), 8.16 (d, J=8.84 Hz, 2H), 8.70 (s, 1H), 11.53 (s, 1H).

Provenance & Evidence