Dimethylformamide → HCID 86752407, compound

Participants

Reaction Steps

To a solution of 2-(3-Amino-2,4-dioxo-5-pyrimidin-2-yl-2,3,4,5-tetrahydro-benzo [b] [1,4]diazepine-1-yl)-N-isopropyl-N-(4-methoxy-phenyl)-acetamide (933 mg, 1.97 mmol) in DMF (20 mL) were added indole-2-carboxylic acid (333 mg, 2.07 mmol), N-hydroxybenzotriazole (266 mg, 1.97 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (415 mg, 2.16 mmol) successively with stirring at ambient temperature. 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 (100 mL), washed with water (2×30 mL), dried over MgSO4, filtered and concentrated under reduced pressure to a give a tan foam. The crude product was purified by flash chromatography on silica gel (30 g) eluting with ethyl acetate (600 mL). Appropriate fractions were combined and concentrated in vacuo to give the title compound (902 mg, 1.46 mmol) as a white foam: 1H NMR (CDCl3, 400 MHz): 9.44 (s 1H), 8.75 (d, 2H, J=4.4 Hz), 7.64-6.88 (m,15H), 5.60 (d, 1H, J=6.8 Hz), 5.03 (m, 1H), 4.45 (d, 1H, J=16.6 Hz), 3.99 (d, 1H, J=16.6 Hz), 3.81 (s, 3H), 1.07 (m, 6H); TLC (CH2Cl2 /CH3OH (19:1)): Rf =0.63; MS (FAB) m/z 618.2 (MH+).

Provenance & Evidence