Sodium hydride → HCID 68411742, compound

Participants

Reaction Steps

tert-Butyl 1-(1-(8-amino-2-oxo-1,2,3,4-tetrahydroquinolin-3-ylamino)-4-methyl-1-oxopentan-2-ylamino)-2-methyl-1-oxopropan-2-ylcarbamate (1.04 g) and 2-(bromomethyl)pyridine hydrobromide (553 mg) were sequentially added to N,N-dimethylformaldehyde (7.5 mL), and sodium hydride (174 mg) was added in two portions to the mixture under cooling on ice, followed by stirring for two hours. The resultant mixture was extracted with ethyl acetate and water, and the aqueous layer was further extracted with ethyl acetate. The organic layers were combined, and the combined organic layer was dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the thus-recovered residue was purified through silica gel column chromatography (hexane:ethyl acetate=1:2), whereby the title compound (393 mg) was yielded.

Provenance & Evidence