1,2-Dichloroethane → N-[(4,6-Dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-propyl-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-propyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (70 mg, 0.283 mmol), DMSO(3 mL), 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone (80 mg, 0.425 mmol), N-methylmorpholine (0.124 mL, 1.132 mmol), 1-hydroxy-7-azabenzotriazole (77 mg, 0.566 mmol), and EDC (109 mg, 0.566 mmol). The collected solid was washed with water and methanol and dried under high vacuum to give 73 mg (68%) of product. LCMS E-S (M+H)=382.3 1H NMR (400 MHz, DMSO-d6) δ ppm 0.82-1.10 (m, 3 H), 1.48 (d, J=6.8 Hz, 6 H), 1.77 (m, 2 H), 2.13 (s, 3 H), 2.21 (s, 3 H), 2.85 (t, J=7.6 Hz, 2 H), 4.36 (d, J=4.8 Hz, 2 H), 5.20 (m, 1 H), 5.90 (s, 1 H), 7.38-7.58 (m, 1 H), 8.26 (s, 1 H), 8.73 (t, J=4.7 Hz, 1 H), 11.57 (br. s., 1 H).

Provenance & Evidence