Triethylamine → HCID 18951104, compound

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Reaction Steps

1 g of triethylamine and 0.49 g of trichloromethyl chloroformate are added, at a temperature close to 0° C., to a solution of 0.72 g of 3-aminoquinoline in 30 cm3 of dichloromethane. The suspension obtained is stirred for 15 minutes at a temperature close to 0° C. and a solution of 1.3 g of tert-butyl 2-(2-amino-N-phenylacetamido)acetate in 10 cm3 of dichloromethane is then added. The reaction mixture is stirred for 3 hours at a temperature close to 20° C. and 20 cm3 of water are then added. The aqueous phase is separated off by decantation and then reextracted with twice 15 cm3 of 1,2-dichloroethane. The organic phases are combined, washed with twice 10 cm3 of water, dried over magnesium sulphate, filtered and then concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. The oil obtained is purified by chromatography on 50 g of silica (0.063-0.2 mm) contained in a column 1.5 cm in diameter [eluent: dichloromethane/methanol (98/2 by volume)], collecting 10-cm3 fractions. The fractions containing only the desired product are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. After recrystallization from ethyl acetate, 0.8 g of tert-butyl 2-{2-[3-(3-quinolyl)ureido]-N-phenylacetamido}acetate melting at 191° C. is obtained.

Provenance & Evidence