Triethylamine → HCID 470751, compound

Participants

Reaction Steps

To a solution of 2-chloro-5,11-dihydro-11-ethyl-5-methyl-8-[2-(2-carboxypyrid-4-yl)ethyl]-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (92 mg, 0.21 mmol) and Et3N (0.03 mL, 0.22 mmol) in t-butanol (20 mL) was added diphenylphosphoryl azide (0.046 g, 0.21 mmol). The reaction mixture was heated at reflux under argon for 16 hours. Solvents were removed by rotary evaporation, and the residue was dissolved in ethyl acetate, washed with saturated aq. sodium bicarbonate, dried (magnesium sulfate), and concentrated. The residue was treated with 2N hydrochloric acid in ethanol at 25°-50° C. for 30 hours. The reaction mixture was concentrated, basified with 6N sodium hydroxide, and extracted with ethyl acetate. Purification by flash chromatography (elution with methanol-dichloromethane) and recrystallization (diethyl ether-petroleum ether) afforded 14 mg (16%) of the title compound, m.p. 95° C. (dec).

Provenance & Evidence