1,2-Dichloroethane → N-[(4,6-Dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-[4-(1H-pyrazol-4-yl)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-(1H-pyrazol-4-yl)phenyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (20 mg, 0.058 mmol), DMSO(1 mL), 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone (16.29 mg, 0.086 mmol), N-methylmorpholine (0.025 mL, 0.230 mmol), 1-hydroxy-7-azabenzotriazole (15.67 mg, 0.115 mmol) and EDC (22.07 mg, 0.115 mmol). The final product was collected as 12 mg (43%). LCMS E-S (M+H)=482.0. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.56 (d, J=6.4 Hz, 6 H), 2.14 (s, 3 H), 2.24 (s, 3 H), 4.42 (d, J=4.8 Hz, 2 H) 5.27-5.47 (m, 1 H), 5.91 (s, 1 H), 7.79 (d, J=8.3 Hz, 2 H), 8.04 (br. s., 1 H), 8.15-8.21 (m, 1 H), 8.27 (d, J=8.3 Hz, 2 H), 8.35-8.42 (m, 1 H), 8.99 (t, J=4.8 Hz, 1 H), 11.58 (br. s., 3 H).

Provenance & Evidence