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 (50 mg, 0.05 mmol) was added to a solution of 7H-indolo[2,1-a][2]benzazepine-6,10-dicarboxamide, 13-cyclohexyl-N6-[2-(diethylamino)-2-oxoethyl]-N10-[(dimethylamino)sulfonyl]-3-methoxy-N6-methyl- (51 mg, 0.08 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-N6-[2-(diethylamino)-2-oxoethyl]-N10-[(dimethylamino)sulfonyl]-6,7-dihydro-3-methoxy-N6-methyl- (44 mg, 0.07 mmol, 86%) as an off-white solid. Partial 1HNMR (300 MHz, CDCl3) δ 11.3 (s, 1H), 8.04 (s, 1H), 7.81 (d, J=8.4 Hz, 1H), 7.69 (d, J=8.4 Hz, 1H), 7.31 (d, J=8.0 Hz, 1H), 6.94-6.86 (m, 2H), 4.80-4.71 (m, 1H), 4.60-4.52 (m, 1), 3.86 (s, 3H), 3.33 (s, 3H), 3.01 (s, 6H). LCMS: m/e 664 (M−H)−, ret time 3.12 min, column A, 4 minute gradient.

Provenance & Evidence