N,N-Dimethylsulfamide → 7H-indolo[2,1-a][2]benzazepine-10-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 7H-indolo[2,1-a][2]benzazepine-10-carboxylic acid, 13-cyclohexyl-6-[[4-(acetyl)-1-piperazinyl]carbonyl] (400 mg, 0.78 mmol), N,N-dimethylsulfamide (390 mg, 3.13 mmol) and DMAP (380 mg, 3.13 mmol) in dimethylacetamide (6 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (450 mg, 2.34 mmol). The reaction solution was stirred at 50° C. for 3 h, concentrated, purified by preparative HPLC (CH3CN/H2O with NH4OAc buffer) to yield 7H-indolo[2,1-a][2]benzazepine-10-carboxamide, 13-cyclohexyl-N-[(dimethylamino)sulfonyl]-6-[[4-(acetyl)-1-piperazinyl]carbonyl] (135 mg, 0.22 mol, 28%) as a yellow powder. 1HNMR (500 MHz, DMSO-d6) δ 11.62 (s, 1H), 8.44 (s, 1H), 7.93 (d, J=8.5 Hz, 1H), 7.65 (d, J=8.5 Hz, 1H), 7.62-7.55 (m, 4H), 7.04 (s, 1H), 5.19 (br s, 1H), 4.34 (br s, 1H), 3.59-3.30 (m, 8H), 2.91 (s, 6H), 2.85-2.75 (m, 1H), 2.10-1.36 (m, 10H), 1.99 (s, 3H). LCMS: m/e 616 (M−H)−, ret time 1.57 min, column A, 2 minute gradient.

Provenance & Evidence