HCID 86672032, compound → HCID 49833677, compound

Participants

Reaction Steps

A solution of phenylmethyl [6-(4-{[2-(3-fluorophenyl)-4-oxopiperidin-1-yl]carbonyl}-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1H-imidazo[4,5-b]pyridin-2-yl]carbamate (0.15 g, 0.24 mmol) in acetic acid (5 mL) was hydrogenated at 1 atm over 10% palladium on carbon (0.15 g) for 18 h. The catalyst was removed by filtration 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-imidazo[4,5-b]pyridin-6-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]carbonyl}-2-(3-fluorophenyl)piperidin-4-one (46 mg, 39% yield) as a pale yellow solid. 1H NMR (400 MHz, CDCl3): 11.44 (bs, 1H), 8.17 (s, 1H), 6.97-7.60 (m, 7H), 6.75 (s, 1H), 5.18 (t, 1H), 4.51-4.66 (m, 2H), 4.13-4.30 (m, 2H), 3.56-3.78 (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 C27H25FN6O3: 501 (MH+)

Provenance & Evidence