Diethylamine → N,N-Diethyl-4-{2-[(5-methyl-furan-2-ylmethyl)-amino]-quinolin-5-yl}-butyramide

Participants

Reaction Steps

Diethylamine (89 mg, 1.22 mmol) was dissolved in 5 mL dioxane. Trimethylaluminium (2M solution in heptane, 0.61 mL, 1.22 mmol) was added and the mixture was stirred for 1 hour at room temperature. 4-{2-[(5-Methyl-furan-2-ylmethyl)-amino]-quinolin-5-yl}-butyric acid methyl ester (137 mg, 0.4 mmol) 7 mL dioxane was added and stirring was continued at 90° C. for 5 hours. The reaction mixture was quenched by addition of 0.6 mL water. The solvent was evaporated off. The residue was purified by flash chromatography on silica gel (heptane/ethyl acetate 100:0->0:100 gradient). The title compound was obtained as a yellow oil (40 mg, 26%), MS: m/e=380.5 (M+H+).

Provenance & Evidence