4-Methylmorpholine → HCID 10051473, compound

Participants

Reaction Steps

To a solution of crude (3S,7S)-3-amino-1-cyclopentyl-7-phenyl-1,3,4,7-tetrahydro-2H-azepin-2-one (8d) (40 mg) in DCM (3 ml) at RT under N2 was added N-[(3,5-difluorophenyl)acetyl]-L-alanine (36 mg), HOBt (40 mg), EDAC.HCl (42 mg), and N-methylmorpholine (15 mg). The reaction was stirred at RT overnight., then diluted with DCM (10 ml) and washed with 1N HCl, 1N K2CO3, dried (Na2SO4), filtered and evaporated. The crude product was purified by flash chromatography (2% MeOH/DCM) to afford the title compound as a 70:30 mixture with N1-[(3R,7R)-1-cyclopentyl-2-oxo-7-phenyl-2,3,4,7-tetrahydro-1H-azepin-3-yl]-N2-[(3,5-difluorophenyl)acetyl]-L-alaninamide as an off white solid (55 mg, 75%). 1H NMR (300 MHz, CDCl3) δ 1.17-2.21 (m, 12H), 2.79-2.87 (m, 1H), 3.55 (s, 2H), 5.44-5.52 (m, 1H), 5.80-5.84 (m, 1H), 5.90-5.93 (s, 1H), 6.26-6.35 (m, 2H), 6.69-6.86 (m, 3H), 7.19-7.46-(m, 6H). MS APCI, m/z=496 (M+1), LC/MS, 2.65 min.

Provenance & Evidence