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

Participants

Reaction Steps

The title compound was prepared in the same manner as described in example 109 using 1-(1-methylethyl)-6-(3-thienyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (70 mg, 0.244 mmol), DMSO (2 mL), 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone (68.9 mg, 0.365 mmol) HCl salt, N-methylmorpholine (0.107 mL, 0.974 mmol), 1-hydroxy-7-azabenzotriazole (33.2 mg, 0.244 mmol) and EDC (93 mg, 0.487 mmol). The final product was collected as 75 mg (73%). LCMS E-S (M+H)=422.2. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.53 (d, J=6.8 Hz, 6H), 2.13 (s, 3H), 2.23 (s, 3H), 4.41 (d, J=4.8 Hz, 2H), 5.30 (quin, J=6.6 Hz, 1H), 5.91 (s, 1H), 7.71 (dd, J=5.0, 3.0 Hz, 1H), 7.92 (d, J=5.0 Hz, 1H), 8.09 (s, 1H), 8.34 (s, 1H), 8.37 (d, J=1.8 Hz, 1H), 8.79-8.95 (m, 1H), 11.58 (s, 1H).

Provenance & Evidence