Tetrahydrofuran → HCID 21830395, compound

Participants

Reaction Steps

A solution of methyl (±)-8-[[[(2-benzimidazolyl)methyl]amino]carbonyl]-2-methyl-3-oxo-2,3,4,5-tetrahydro-1H-2-benzazepine-4-acetate (0.10 g, 0.24 mmol), LiOH.H2O (0.013 g, 0.31 mmol), THF (2 mL), and H2O (2 mL) was stirred at RT for 18 h, then was concentrated to dryness. The residue was dissolved in H2O, and the solution was brought to pH 4-5 with 3N HCl. The resulting precipitate was collected by filtration and dried. Recrystallization from boiling isopropanol gave the title compound (0.035 g, 36%) as a colorless solid: 1H NMR (DMSO-d6) δ 9.13 (t, J=5.7 Hz, 1H), 7.79 (m, 1H), 7.48 (m, 2H), 7.23 (d, J=7.9 Hz, 1H), 7.14 (m, 2H), 5.32 (d, J=16.9 Hz, 1H), 4.69 (d, J=5.7 Hz, 2H), 4.03 (d, J=16.7 Hz, 1H), 3.79 (m, 1H), 3.14 (dd, J=18, 2 Hz, 1H), 2.90 (s, 3H), 2.70 (m, 2H), 2.38 (dd, J=11.4, 3 Hz, 1H); MS (ES) m/e 407 (M+H)+. Anal. Calcd for C22H22N4O4.1.5 H2O.0.5 C3H8O: C, 60.90; H, 6.31; N, 12.09. Found: C, 60.68; H, 6.05; N, 12.05.

Provenance & Evidence