1,2-Dichloroethane → (4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl 6-cyclopropyl-1-[2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)ethyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

Participants

Reaction Steps

To a solution of DMSO (10 mL) were sequentially added 6-cyclopropyl-1-[2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)ethyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (270 mg, 0.779 mmol), 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone (178 mg, 1.169 mmol), and 1-hydroxy-7-azabenzotriazole (212 mg, 1.559 mmol), and the mixture stirred at room temperature for 10 min. Next was added EDC (299 mg, 1.559 mmol) and N-methylmorpholine (0.343 mL, 3.12 mmol), and reaction mixture was stirred at room temperature for 16 h. The contents were diluted with water (25 mL) and stirred for 10 min. The solid product was filtered off, dried, and collected as 0.290 g (98%). LCMS E-S (M+H)=381.2. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.00-1.15 (m, 4 H), 1.30 (s, 9H), 2.13 (s, 3 H), 2.18-2.32 (m, 4 H), 4.36 (d, J=4.80 Hz, 2 H), 4.42 (t, J=5.81 Hz, 2 H), 5.90 (s, 1 H), 6.85 (t, J=5.56 Hz, 1 H), 7.44 (s, 1 H), 8.22 (s, 2 H), 8.73 (t, J=4.67 Hz, 1 H), 11.57 (br. s., 1 H).

Provenance & Evidence