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

Participants

Reaction Steps

6-Chloro-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (0.12 g, 0.501 mmol), 1-hydroxy-7-azabenzotriazole (0.102 g, 0.751 mmol), EDC (0.144 g, 0.751 mmol), and 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone (0.123 g, 0.651 mmol) were dissolved in dimethyl sulfoxide (3.0 mL) and stirred at room temperature. Added next to the stirring contents was N-methylmorpholine (0.220 mL, 2.003 mmol) via syringe at once. After stirring at room temperature overnight, the reaction mixture was slowly added to water (75 mL) and stirred for 10 min. After sitting for 10 min. at room temperature, the contents were filtered to afford a tan solid which was washed with water and then cold 50% aq EtOH. The contents were filtered, air-dried for 10 min., and then dried under vacuum for 1 hr. The collected solid was then further dried in a vacuum oven at 45° C. for 4 hr. The title compound was collected as 0.105 g (55%). LCMS E-S (M+H)=373.9. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.49 (d, J=6.82 Hz, 6H), 2.13 (s, 3H), 2.20 (s, 3H), 4.35 (d, J=4.80 Hz, 2H), 5.07-5.20 (m, 1H), 5.89 (s, 1H), 7.66 (s, 1H), 8.39 (s, 1H), 8.91 (t, J=4.80 Hz, 1H), 11.55 (s, 1H).

Provenance & Evidence