N-Methylethylenediamine → HCID 19592700, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-chloromethyl-8-(2,6-dichlorobenzoylamino)-3-ethylquinoline (150 mg) and N-methylethylenediamine (141 mg) in 1,2-dimethoxyethane was stirred for 2 hours at 70° C. The mixture was partitioned between dichloroethane and water, and the organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo to give a residue containing 8-(2,6-dichlorobenzoylamino)-3-ethyl-4-[(2-methylaminoethyl-amino)methyl]quinoline. To the solution of the obtained residue in 1,3-dimethyl-2-imidazolidinone was added 1,1'-carbonyldiimidazole (309 mg), and the mixture was stirred for 30 minutes at 70° C., for 1 hour at 100° C. and for 1 hour at 150° C. Water was added to the mixture, and the resulting precipitates were collected by filtration. The residue was purified by preparative thin layer chromatography (methanol-dichloromethane) and crystallized from isopropyl alcohol to give 8-(2,6-dichlorobenzoylamino)-3-ethyl-4-(3-methyl-2-oxoimidazolidin-1-ylmethyl)quinoline (28.6 mg).

Provenance & Evidence