Dimethylacetamide → Piperazine-1-carboxylic acid

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a stirred solution of 7H-indolo[2,1-a][2]benzazepine-10-carboxylic acid, 13-cyclohexyl-6-[[4-[(1,1-dimethylethoxy)carbonyl]-1-piperazinyl]carbonyl] (100 mg, 0.18 mmol), N,N-dimethylsulfamide (110 mg, 0.89 mmol) and DMAP (110 mg, 0.90 mmol) in dimethylacetamide (2 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (135 mg, 0.71 mmol). The reaction solution was stirred at 50° C. overnight, concentrated, purified by preparative HPLC (MeOH/2O with NH4OAc buffer) to yield 1-piperazinecarboxylic acid, 4-[[13-cyclohexyl-10-[[[(dimethylamino)sulfonyl]amino]carbonyl]-7H-indolo[2,1-a][2]benzazepin-6-yl]carbonyl]-, 1,1-dimethylethyl ester (49 mg, 0.073 mol, 40%) as a yellow solid. 1H NMR (500 MHz, CDCl3) δ 8.10 (s, 1H), 7.91 (d, J=8.6 Hz, 1H), 7.58 (br d, J=7.6 Hz, 1H), 7.63-7.46 (m, 3H), 7.40 (br d, J=7.3 Hz, 1H), 6.87 (s, 1H), 5.15 (br s, 1H), 4.37 (br s, 1H), 3.56-3.22 (m, 8H), 3.06 (s, 6H), 2.89-2.81 (m, 1H), 2.15-1.15 (m, 10H), 1.44 (s, 9H). LCMS: m/e 676 (M+H)+, ret time 2.05 min, column B, 2 minute gradient.

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