Cyclohexylamine → N-Cyclohexyl-2-[(3,5-dichloropyridin-4-yl)amino]-7,7-dimethyl-7,8-dihydro-1H-furo[3,2-e]benzimidazole-5-carboxamide

Participants

Reaction Steps

To a solution 2-[(3,5-dichloropyridin-4-yl)amino]-7,7-dimethyl-7,8-dihydro-1H-furo[3,2-e]benzimidazole-5-carboxylic acid (Intermediate-3, 0.050 g, 0.127 mmol) in mixture of DMF (0.5 mL) and THF (3.0 mL), were added O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (0.082 g, 0.255 mmol, TBTU), N-methyl morpholine (1.0 mL). The reaction mass was stirred at RT for 30 minutes. Then to the reaction mass added cyclohexyl amine (0.020 g, 0.202 mmol). The reaction mass was stirred at RT for 14-16 h. The reaction mass was quenched in water and extracted with ethyl acetate. The organic layer was washed with sodium bicarbonate and dilute HCl solution, and dried over anhydrous sodium sulphate and concentrated to afford 0.005 g of the desired product. 1HNMR (DMSO-d6): δ 1.15-1.35 (m, 7H), 1.48 (s, 3H), 1.58 (m, 2H), 1.79 (m, 2H), 3.00-3.07 (m, 4H), 3.80 (m, 1H), 7.20 (s, 1H), 7.66 (d, J=7.5 Hz, 1H), 8.41 (s, 2H), 10.89 (s, 1H), 11.39 (s, 1H); MS [M−H]−: 472.43.

Provenance & Evidence