Hydrochloric Acid → 7H-indolo[2,1-a][2]benzazepine-10-carboxylic acid

Participants

Reaction Steps

Added 1M NaOH (aq.) (0.5 mL, 0.5 mmol) to a solution of methyl 7H-indolo[2,1-a][2]benzazepine-10-carboxylate, 13-cyclohexyl-3-methoxy-6-[[[2-(methylamino)-2-oxoethyl]amino]carbonyl]- (140 mg, 0.27 mmol) in THF/MeOH (1:1, 3 mL) and heated the reaction mixture in a sealed tube with microwave irradiation at 80° C. for 20 min., then at 85° C. for 10 min. The reaction was cooled, neutralized with 1M HCl (aq.) (0.5 mL, 0.5 mmol) and concentrated to remove organic solvents. The residue was slurried with H2O and the solids were collected by filtration, flushed with H2O and dried to yield 7H-indolo[2,1-a][2]benzazepine-10-carboxylic acid, 13-cyclohexyl-3-methoxy-6-[[[2-(methylamino)-2-oxoethyl]amino]carbonyl]- (123 mg, 0.25 mmol, 90%) as a yellow solid. 1HNMR (500 MHz, CD3OD) δ 8.30 (s. 1H), 7.87 (d, J=8.5 Hz, 1H), 7.70 (d, J=8.5 Hz, 1H), 7.62 (s, 1H), 7.60 (d, J=8.5 Hz, 1H), 7.20 (d, J=8.5 Hz, 1H), 7.15 (s, 1H), 5.74-5.60 (m, 1H), 4.24-4.11 (m, 1H), 4.02-3.88 (m, 2H), 3.95 (s, 3H), 2.95-2.84 (m, 1H), 2.75 (s, 3H), 2.22-1.17 (m, 10H). LCMS: m/e 500 (M−H)−, ret time 1.38 min, column A, 3 minute gradient.

Provenance & Evidence