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 (77 mg, 0.07 mnol) 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-methoxyethyl)-N6-methyl- (65 mg, 0.11 mmol) in MeOH/CH2Cl2 (1:1, 4 mL) and the reaction mixture was vacuum flushed with nitrogen (3×) and then with hydrogen (3×). The reaction 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-methoxyethyl)-N6-methyl- (60 mg, 0.10 mmol, 92%) as a light yellow solid. Mixture of atrope diastereomers. 1HNMR (300 MHz, CD3OD) δ 8.10-7.92 (m, 1H), 7.91-7.83 (m, 1H), 7.62-7.51 (m, 1H), 7.42-7.33 (m, 1H), 7.10-6.84 (m, 2H), 4.67-4.44 (m, 1H), 3.93-3.86 (m, 3H), 3.84-3.21 (m, 1H), 3.06-2.86 (m, 8H), 2.83-2.64 (m, 2H), 2.18-1.19 (m, 10H). LCMS: m/e 611 (M+H)+, ret time 2.12 min, column C, 2 minute gradient.

Provenance & Evidence