7H-indolo[2,1-a][2]benzazepine-6,10-dicarboxamide → 5H-indolo[2,1-a][2]benzazepine-6,10-dicarboxamide

Participants

Reaction Steps

10% Palladium on carbon (38 mg, 0.04 mmol) was added to a solution of 7H-indolo[2,1-a][2]benzazepine-6,10-dicarboxamide, 13-cyclohexyl-N10-[(dimethylamino)sulfonyl]-3-methoxy-N6-[2-[(2-methoxyethyl)amino]-2-oxoethyl]-N6-methyl- (40 mg, 0.06 mmol) in MeOH (2 mL) and the reaction mixture was vacuum flushed with nitrogen (3×) and then with hydrogen (3×). The reaction mixture was stirred under a balloon of hydrogen overnight, filtered through a pad of celite and concentrated to yield 5H-indolo[2,1-a][2]benzazepine-6,10-dicarboxamide, 13-cyclohexyl-N10-[(dimethylamino)sulfonyl]-6,7-dihydro-3-methoxy-N6-[2-[(2-methoxyethyl)amino]-2-oxoethyl]-N6-methyl- (30 mg, 0.04 mmol, 75%) as a yellow solid. Diastereomeric mixture of atrope isomers with amide rotamers: Partial 1HNMR (300 MHz, CDCl3) δ 11.30 (br s, 0.2H), 11.00 (br s, 0.5H), 8.35 (br s, 90% H2Õ0.1% TFA, Solvent B=90% MeO{tilde over (H)}10% H2Õ0.1% TFA, Start % B=0, Final % B=100, Gradient time=2 min, Flow Rate=5 ml/min, Column: Xterra MS C18 S7 3.0×50 mm; LC/MS: (ES+) m/z (M+H)+=528.23, HPLC Rt=2.040 min. 0.2H), 7.98 (br s, 0.6H), 7.89-7.66 (m, 2H), 7.37-7.28 (m, 1H), 6.95-6.85 (m, 2H), 6.10-6.00 (m, 0.5H), 5.08-4.98 (m, 0.4H), 3.86 (s, 3H), 3.01 (s, 6H). LCMS: m/e 666 (M−H)−, ret time 2.74 min, column A, 4 minute gradient.

Provenance & Evidence