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

Participants

Reaction Steps

To a 4 mL solution of DMSO were sequentially added 6-cyclopropyl-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (0.11 g, 0.448 mmol), 3-(aminomethyl)-6-cyclopropyl-4-methyl-2(1H)-pyridinone hydrochloride (0.106 g, 0.493 mmol), 1-hydroxy-7-azabenzotriazole (0.073 g, 0.538 mmol), EDC (0.103 g, 0.538 mmol), and then N-methylmorpholine (0.197 mL, 1.79 mmol) via syringe. After stirring overnight at room temperature, the suspension was diluted with 50 mL of water and stirred for 15 min. After standing at room temperature for 15 min., the reaction mixture was filtered and the collected solid washed with additional water. The solid was then dried in a vacuum oven at 45° C. for 4 h. The product was obtained as 0.165 g (89%). LCMS E-S (M+H)=406.5. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.76-0.82 (m, 2 H), 0.91-0.98 (m, 2 H), 1.03-1.12 (m, 4 H), 1.46 (d, J=6.82 Hz, 6 H), 1.74-1.84 (m, 1 H), 2.19 (s, 3 H), 2.21-2.31 (m, 1 H), 4.34 (d, J=5.05 Hz, 2 H), 5.05-5.18 (m, 1 H), 5.73 (s, 1 H), 7.42 (s, 1 H), 8.21 (s, 1 H), 8.72 (t, J=4.93 Hz, 1 H), 11.61 (br. s., 1 H).

Provenance & Evidence