1,2-Dichloroethane → N-[(4,6-Dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-[4-(methylsulfonyl)phenyl]-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-[4-(methylsulfonyl)phenyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (90 mg, 0.250 mmol), DMSO (2 mL), 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone (70.9 mg, 0.376 mmol), N-methylmorpholine (0.110 mL, 1.002 mmol), 1-hydroxy-7-azabenzotriazole (68.2 mg, 0.501 mmol) and EDC (96 mg, 0.501 mmol). The final product was collected as 106 mg (85%). LCMS E-S (M+H)=494.2. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.56 (d, J=5.6 Hz, 6H), 2.13 (br. s., 3H), 2.23 (br. s., 3H), 4.42 (m, 2H), 5.36 (br. s., 1H), 5.91 (br. s., 1H), 8.11 (d, J=7.3 Hz, 2H), 8.27 (br. s., 1H), 8.39-8.64 (m, 3H), 9.01 (br. s., 1H), 11.58 (br. s., 1H).

Provenance & Evidence