Trifluoroacetic acid → HCID 69522037, compound

Participants

Reaction Steps

A solution of N-t-butyloxycarbonyl-(3R)-3-amino-2-oxo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepine (40.0 mg, 0.114 nmol) in dimethylformamide (1.5 mL) was stirred with sodium hydride (6.83 mg, 0.17 mmol, 60% dispersion in oil) for 15 min, then N-(4-bromobutyl)-phthalimide (32.1 mg, 0.114 mmol) was added. The reaction was stirred overnight and worked up with methylene chloride and water. The crude product was dissolved in methylene chloride (4.5 mL) containing trifluoroacetic acid (1.5 mL) and stirred for 1 h. The solvents were removed in vacuo, and the crude product dissolved in tetrahydrofuran (1 mL) along with p-nitrochloroformate (14.5 mg, 0.072 mmol) and triethylamine (0.20 mL, 0.14 mmol). After stirring for 2 h, 3-(4-piperidinyl)-3,4-dihydroquinazolin-2(1H)-one hydrochloride (19.3 mg, 0.072 mmol) and triethylamine (0.020 mL, 0.14 nmol) was added and the reaction 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 yield the title compound (19 mg). MS 710.3123 (M+1)

Provenance & Evidence