1,2-Dichloroethane → 6-(4-Chlorophenyl)-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-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 6-(4-chlorophenyl)-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (70 mg, 0.222 mmol), DMSO(2 mL), 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone HCl salt (62.7 mg, 0.333 mmol), N-methylmorpholine (0.097 mL, 0.887 mmol), 1-hydroxy-7-azabenzotriazole (60.3 mg, 0.443 mmol) and EDC (85 mg, 0.443 mmol). The final product was collected as 77 mg (78%). LCMS E-S (M+H)=450.3. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.55 (d, J=6.6 Hz, 6 H), 2.13 (s, 3 H), 2.22 (s, 3 H), 4.41 (d, J=4.6 Hz, 2 H), 5.34 (quin, J=6.7 Hz, 1 H), 5.91 (s, 1 H), 7.64 (d, J=8.6 Hz, 2 H), 8.19 (s, 1 H), 8.31 (d, J=8.6 Hz, 2 H), 8.39 (s, 1 H), 8.97 (t, J=4.7 Hz, 1 H), 11.58 (s, 1 H).

Provenance & Evidence