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

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 7H-indolo[2,1-a][2]benzazepine-10-carboxylic acid, 13-cyclohexyl-3-methoxy-6-[[[2-(dimethylamino)-2-oxoethyl]methylamino]carbonyl]- (53 mg, 0.10 mmol), N,N-dimethylsulfamide (62 mg, 0.50 mmol) and DMAP (61 mg, 0.50 mmol) in dimethylacetamide (1.5 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (76 mg, 0.40 mmol). The reaction solution was stirred at 50° C. for 5 h, concentrated under a steam of nitrogen, diluted with MeOH (1 mL) and purified by preparative HPLC (CH3CN/H2O with TFA buffer) to yield 7H-indolo[2,1-a][2]benzazepine-6,10-dicarboxamide, 13-cyclohexyl-N6-[2-(dimethylamino)-2-oxoethyl]-N10-[(dimethylamino)sulfonyl]-3-methoxy-N6-methyl- (13 mg, 0.02 mmol, 20%) as a yellow solid. 1HNMR (500 MHz, CD3OD) δ 8.19 (s, 0.5H), 8.12 (s, 0.5H), 7.91 (d, J=8.1 Hz, 1H), 7.63 (d, J=8.1 Hz, 1H), 7.60-7.50 (m, 1H), 7.20-6.93 (m, 3H), 5.14 (br s, 1H), 4.46-4.11 (m, 2H), 3.96-3.87 (m, 1H), 3.93 (s, 3H), 3.12-2.86 (m, 13H), 2.45 (br s, 3H), 2.20-1.74 (m, 6H), 1.57-1.19 (m, 4H). LCMS: m/e 636 (M+H)+, ret time 2.82 min, column B, 3 minute gradient.

Provenance & Evidence