1,2-Dichloroethane → 6-Cyclopropyl-1-(1-cyclopropylethyl)-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

Participants

Reaction Steps

6-Cyclopropyl-1-(1-cyclopropylethyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (186 mg, 0.652 mmol), 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone (160 mg, 0.847 mmol), 1-hydroxy-7-azabenzotriazole (177 mg, 1.304 mmol), EDC (250 mg, 1.304 mmol) and N-methylmorpholine (0.287 mL, 2.61 mmol) were dissolved in DMSO (10 mL) and stirred at room temperature for 3 days. The reaction mixture was diluted with water (25 mL), stirred, and filtered. The product was dried and collected as a solid, 0.200 g (73%). LCMS E-S (M+H)=420.0. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.14-0.30 (m, 2H), 0.32-0.43 (m, 1H), 0.48-0.64 (m, 1H), 0.89-1.11 (m, 4H), 1.22-1.43 (m, 1H), 1.55 (d, J=6.82 Hz, 3H), 2.11 (s, 3H), 2.18-2.28 (m, 4H), 2.37 (s, 3H), 4.05-4.21 (m, 1H), 4.34 (d, J=4.80 Hz, 2H), 5.87 (s, 1H), 6.99 (s, 1H), 8.59 (t, J=4.67 Hz, 1H), 11.51 (br. s., 1H).

Provenance & Evidence