Tetrahydrofuran → HCID 11707040, compound

Participants

Reaction Conditions

Reaction Steps

3-Amino-2-oxo-5-phenyl-1-(2,2,2-trifluoroethyl)-2,3-dihydro-1H-1,4-benzodiazepine (20.0 mg, 0.06 mmol) (Y.-J. Shi et al., Tetrahedron, 1999, 55, 909-918) and p-nitrophenylchloroformate (12.1 mg, 0.06 mmol) were dissolved in tetrahydrofuran (0.5 mL) under argon, and cooled to 0° C. Triethylamine (19 uL, 0.14 mmol) was added and the reaction stirred for 1 h, followed by addition of more triethylamine (19 uL) and 4-phenyl-1-piperidin-4-yl-1,3-dihydro-2H-imidazol-2-one hydrochloride (16.8 mg, 0.06 mmol), prepared according to the procedure described in the patent U.S. Pat. No. 6,344,449 B1. The reaction was warmed to room temperature and stirred overnight. The crude product was purified by reverse phase HPLC (C-18, 5% to 95% 0.1% trifluoroacetic acid/acetonitrile in 0.1% aqueous trifluoroacetic acid gradient elution) to give she title compound (26.1 mg). MS 603 (M+1)

Provenance & Evidence