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

Participants

Reaction Conditions

Reaction Steps

To a solution of 7H-indolo[2,1-a][2]benzazepine-10-carboxylic acid, 13-cyclohexyl-6-[[[2-(dimethylamino)-2-oxoethyl]methylamino]carbonyl]- (180 mg, 0.36 mmol), N,N-dimethylsulfamide (134 mg, 1.08 mmol) and DMAP (122 mg, 1.08 mmol) in dimethylformamide (2 mL) was added PS-carbodiimide (830 mg, 1.3 mmol/g, 1.08 mmol). The reaction solution was shaken at 45° C. overnight, filtered, concentrated and purified by preparative HPLC (MeOH/H2O with an NH4OAc buffer) to yield 7H-indolo[2,1-a][2]benzazepine-6,10-dicarboxamide, 13-cyclohexyl-N6-[2-(dimethylamino)-2-oxoethyl]-N10-[(dimethylamino)sulfonyl]-N6-methyl- (90 mg, 0.15 mmol, 41%) as a yellow solid. 1HNMR (300 MHz, CDCl3) δ 8.12 (br s. 1H), 7.88 (d, J=8.8 Hz, 1H), 7.71-7.52 (m, 2H), 7.50-7.35 (m, 3H), 6.86 (s, 1H), 5.15-5.01 (m, 1H), 4.67-4.51 (m, 1H), 3.79-3.62 (m, 1H), 3.14-2.92 (m, 12H), 2.88-2.75 (m, 1H), 2.48 (br s, 3H), 2.10-1.65 (m, 6H), 1.55-1.08 (m, 4H). LCMS: m/e 604 (M−H)−, ret time 2.57 min, column A, 4 minute gradient.

Provenance & Evidence