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-N10-[(dimethylamino)sulfonyl]-N6,N6-bis(2-hydroxyethyl)-3-methoxy- (47 mg, 0.08 mmol) in MeOH (3 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. Additional 10% palladium on carbon (30 mg, 0.03 mmol) was added and the reaction mixture was once again 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-N11-[(dimethylamino)sulfonyl]-6,7-dihydro-N6,N6-bis(2-hydroxyethyl)-3-methoxy- (39 mg, 0.06 mmol, 83%) as a yellow solid. Mixture of atrope diasteromers: 1HNMR (300 MHz, CD3OD) δ 8.13-7.93 (m, 1H), 7.88-7.79 (m, 1H), 7.66-7.58 (m, 1H), 7.40-7.31 (m, 1H), 7.06-6.88 (m, 2H), 4.56-4.34 (m, 2H), 3.94-3.86 (m, 3H), 3.85-3.64 (m, 8H), 3.48-3.37 (m, 1H), 3.03-2.82 (m, 2H), 2.99 (s, 6H), 2.77-2.63 (m, 1H), 2.19-1.17 (m, 10H). LCMS: m/e 625 (M−H)−, ret time 2.44 min, column A, 4 minute gradient.

Provenance & Evidence