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

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Reaction Steps

A mixture of 1-(1-methylethyl)-6-(4-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (169 mg, 0.6 mmol), 3-(aminomethyl)-4-cyclohexyl-6-methyl-2(1H)-pyridinone trifluoroacetate (221 mg, 0.660 mmol), EDC (150 mg, 0.780 mmol), HOAT (106 mg, 0.780 mmol), and N-methylmorpholine (0.264 mL, 2.400 mmol) in DMF (3 mL) were stirred at room temperature for 6 days. water (15 mL) was added to the slurry, and it was stirred for an hour. The precipitate was then collected by vacuum filtration and rinsed with EtOH (4 mL), and the solid was dried in the vacuum oven overnight to give the title compounds as an off-white solid (137 mg, 45%). LCMS E-S (M+H)=485.2. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.09-1.44 (m, 5H), 1.56 (d, J=6.57 Hz, 6H), 1.55-1.72 (m, 5H), 2.15 (s, 3H), 2.80-2.92 (m, 1H), 4.53 (d, J=4.55 Hz, 2H), 5.36 (spt, J=6.53 Hz, 1H), 6.03 (s, 1H), 8.18-8.23 (m, 2H), 8.26 (s, 1H), 8.45 (s, 1H), 8.75-8.82 (m, 2H), 9.01 (t, J=4.55 Hz, 1H), 11.59 (s, 1H).

Provenance & Evidence