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

Participants

Reaction Conditions

Reaction Steps

Methyl 7H-indolo[2,1-a][2]benzazepine-10-carboxylate, 13-cyclohexyl-3-methoxy-6-[[[2-(dimethylamino)-2-oxoethyl]methylamino]carbonyl]- (117 mg, 0.21 mmol) was dissolved into THF/MeOH (1:1, 2 mL) and 1M NaOH (aq.) (0.5 mL, 0.5 mmol). The reaction mixture was heated in a sealed tube with microwave irradiation at 85° C. for 20 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 purified by preparative HPLC to yield 7H-indolo[2,1-a][2]benzazepine-10-carboxylic acid, 13-cyclohexyl-3-methoxy-6-[[[2-(dimethylamino)-2-oxoethyl]methylamino]carbonyl]- (71 mg, 0.13 mmol, 63%) as a yellow solid. Mixture of amide rotamers: 1HNMR (500 MHz, CD3OD) δ 8.24 (br s, 1H), 7.88 (d, J=8.4 Hz, 1H), 7.71 (d, J=8.4 Hz, 1H), 7.56 (d, J=8.4 Hz, 1H), 7.18-6.88 (m, 2H), 7.14 (dd, J=8.4, 2.2 Hz, 1H), 5.14 (br s, 1H), 4.49-4.12 (m, 2H), 3.97-3.88 (m, 1H), 3.93 (s, 3H), 3.15-2.83 (m, 7H), 2.56 (s, 1.5H), 2.42 (s, 1.5H), 2.23-1.73 (m, 6H), 1.59-1.17 (m, 4H). LCMS: m/e 530 (M+H)+, ret time 1.40 min, column A, 2 minute gradient.

Provenance & Evidence