Ethanol → N-[(4,6-Dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-(1-piperidinyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a 10 mL reaction vial containing stir bar were added 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 (0.060 g, 0.160 mmol), ethanol (1.5 mL), and then piperidine (0.318 mL, 3.21 mmol) via syringe at once. The contents were capped, placed into a heat block, and heated at 120° C. for 18 h. After cooling to room temperature, the reaction mixture was diluted with water (40 mL), adjusted to pH 6-7, and stirred for 15 min. The contents were filtered and washed with water. The product was dried in vacuum oven at 50° C. for 5 hr. The product was obtained as 57 mg (82%). LCMS E-S (M+H)=422.8. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.43 (d, J=6.82 Hz, 6H), 1.53-1.67 (m, 6H), 2.12 (s, 3H), 2.20 (s, 3H), 3.61-3.73 (m, 4H), 4.34 (d, J=5.05 Hz, 2H), 4.91-5.04 (m, 1H), 5.89 (s, 1H), 7.10 (s, 1H), 7.97 (s, 1H), 8.65 (t, J=4.93 Hz, 1H), 11.51 (br. s., 1H).

Provenance & Evidence