Potassium Carbonate → 2-(4-fluorophenyl)-1-({7-[4-(1H-imidazol-2-yl)phenyl]-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl}carbonyl)piperidin-4-one

Participants

Reaction Steps

To a solution of 2-methylpropyl 2-[4-(4-{[2-(4-fluorophenyl)-4-oxopiperidin-1-yl]carbonyl}-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)phenyl]-1H-imidazole-1-carboxylate (0.27 g, 0.44 mmol) in methanol (50 mL) was added potassium carbonate (0.37 g, 2.65 mmol) at 0° C. and the reaction mixture was stirred for 2 hours at room temperature. The solid was filtered off and the pH of the resulting solution was adjusted to 6-7 by addition of glacial acetic acid. The solvent was evaporated and the residue was dissolved in ethyl acetate (250 mL), washed with saturated aqueous sodium bicarbonate (2×50 mL), brine and dried over anhydrous sodium sulfate, filtered and concentrated. The precipitating product was collected by filtration, washed with hexane and dried to give 2-(4-fluorophenyl)-1-({7-[4-(1H-imidazol-2-yl)phenyl]-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl}carbonyl)piperidin-4-one (0.19 g, 86%). 1H NMR (400 MHz, d6-DMSO): 12.48 (s, 1H), 8.00 (d, 2H), 7.68 (d, 2H), 7.61 (d, 1H), 7.55 (dd, 1H), 7.31-7.26 (m, 3H), 710-6.92 (m, 4H), 5.20 (t, 1H), 4.59 (s, 2H), 4.23 (m, 2H), 3.73-3.63 (m, 3H), 3.31 (m, 1H), 2.85 (m, 2H), 2.61 (m, 1H), 2.30 (2t, 1H). MS (EI) for C30H27FN4O3: 511 (MH+).

Provenance & Evidence