HCID 86672028, compound → HCID 49833507, compound

Participants

Reaction Steps

A solution of phenylmethyl [6-(4-{[2-(3,4-difluorophenyl)-4-oxopiperidin-1-yl]carbonyl}-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1H-benzimidazol-2-yl]carbamate (0.11 g, 0.17 mmol) in acetic acid (5 mL) was hydrogenated at 1 atm over 10% Pd—C (0.1 g) for 2 h. The catalyst was filtered off and the filtrate was concentrated. The resulting brown residue was dissolved in methanol and purified by preparative reverse phase HPLC to afford 1-{[7-(2-amino-1H-benzimidazol-6-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]carbonyl}-2-(3,4-difluorophenyl)piperidin-4-one (0.007 g, 8% yield) as a pale yellow solid. 1H NMR (400 MHz, CDCl3): 7.02-7.29 (m, 8H), 6.98 (d, 1H), 6.94 (d, 1H), 5.27 (t, 1H), 4.43-4.46 (m, 2H), 4.16-4.30 (m, 2H), 3.70-3.85 (m, 3H), 3.21-3.31 (m, 1H), 2.79-2.99 (m, 2H), 2.51-2.61 (m, 1H), 2.32 (d, 1H); MS (EI) for C28H25F2N5O3: 518 (MH+).

Provenance & Evidence