Dimethylformamide → 1H-Indole-2-carboxylic acid {1-[isopropyl-(4-methoxyphenyl)-carbamoylmethyl]-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl}-amide

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Reaction Steps

To a solution of 2-(3-Amino-2,4-dioxo-2,3,4,5-tetrahydro-benzo[b][1,4]-diazepin-1-yl)-N-isopropyl-N-(4-methoxyphenyl)-acetamide (350 mg, 0.883 mmol) in DMF (10 mL) were added indole-2-carboxylic acid (142 mg, 0.883 mmol), N-hydroxybenzotriazole (119 mg, 0.883 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (169 mg, 0.883 mmol) successively with stirring. The resultant mixture was stirred at ambient temperature for 18 hours. The solvent was evaporated under reduced pressure to give a yellow oil which was dissolved in ethyl acetate (60 mL), washed with water (20 mL) and brine (20 mL), dried over MgSO4, filtered and concentrated under reduced pressure to a yellow oil which solidified on standing. The crude product was triturated with boiling ethanol (20 mL), cooled, filtered, and dried to give the title compound (169 mg, 0.313 mmol) as a yellow solid: 1H NMR (300 MHz, Acetone-d6): d 10.85 (br s, 1H), 9.83 (brs, 1H), 7.67 (m, 2H), 7.53 (m, 2H), 7.37-7.20 (m, 7H), 7.04 (m, 3H), 5.28 (d, J=7.5 Hz, 1H), 4.87 (m, 1H), 4.31 (d, J=16.3 Hz, 1H), 4.13 (d, J=16.6 Hz, 1H), 3.83 (s, 3H), 1.02 (m, 6H); TLC (CH2Cl2 /CH3OH (19:1)): Rf =0.24; MS (FAB): m/z=540 (MH+).

Provenance & Evidence