Triethylamine → HCID 14651214, compound

Participants

Reaction Steps

A mixture of 0.50 g (1.60 mmol) of 8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-5-methyl-4-oxo-3-quinolinecarboxylic acid, 0.36 g (1.93 mmol) of 3-(t-butoxycarbonyl) aminopyrrolidine, 0.48 g (4.75 mmol) of triethylamine, and 20 mL of acetonitrile was refluxed for 4 hours, then stirred at room temperature overnight. The solution was concentrated and the residue was triturated with ether:hexane (1:1) and filtered. The solid was washed with water and hexane. The crude product was suspended in 15 mL of dichloromethane and 1.5 mL of trifluoroacetic acid and was stirred at room temperature for 4 hours. The solution was concentrated to a gold solid which was suspended in water, made basic (pH 11) with 10% sodium hydroxide, and filtered. The solution was then neutralized (pH 7.1), and the precipitate was collected by filtration, washed with water, and dried in vacuo to give 0.29 g of the title compound, mp 124°-126° C.

Provenance & Evidence