Tert-Butylamine → N-tert-Butyl-2-(3-ethynyl-quinolin-6-yloxy)-2-methylsulfanyl-acetamide

Participants

Reaction Steps

(3-Ethynyl-quinolin-6-yloxy)-methylsulfanyl-acetic acid (1.1 g), N-tert-Butyl amine (0.467 ml), 1-hydroxy-7-azabenzotriazole (HOAT) (0.602 mg), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDCl) (849 mg) and triethylamine (0.84 ml) in dry N,N-dimethylformamide (20 ml) were stirred at ambient temperature for 16 hours. The reaction mixture was diluted with ethyl acetate and poured on 60 ml aq. sat. sodium hydrogen carbonate. The water phase was extracted with 3×150 ml ethyl acetate. All organic layers were combined, dried over sodium sulfate, filtered and evaporated. The residue was purified by column chromatography (heptane/ethyl acetate 13:7) to give N-tert-Butyl-2-(3-ethynyl-quinolin-6-yloxy)-2-methylsulfanyl-acetamide (1.11 g) as yellowish solid.

Provenance & Evidence