1,2-Dichloroethane → N-[(4,6-Dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-[4-(methyloxy)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-(methyloxy)phenyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (70 mg, 0.225 mmol), DMSO (3 mL), 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone (63.6 mg, 0.337 mmol) HCl salt, N-methylmorpholine (0.099 mL, 0.899 mmol), 1-hydroxy-7-azabenzotriazole (61.2 mg, 0.450 mmol), and EDC (86 mg, 0.450 mmol). The final product was collected as 89 mg (89%). LCMS E-S (M+H)=446.5. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.54 (d, J=6.8 Hz, 6H), 2.13 (s, 3H), 2.23 (s, 3H), 3.85 (s, 3H), 4.41 (d, J=4.8 Hz, 2H), 5.20-5.48 (m, 1H), 5.91 (s, 1H), 7.11 (d, J=8.8 Hz, 2H), 8.11 (s, 1H), 8.24 (d, J=8.8 Hz, 2H), 8.34 (s, 1H), 8.95 (m, 1H), 11.58 (s, 1H).

Provenance & Evidence