1,1'-Carbonyldiimidazole → HCID 19592370, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-chloro-8-(2,6-dichlorobenzoylamino)quinoline (400 mg) and N-benzylethylenediamine (854 mg) was stirred for 6 hours at 130° C. The mixture was partitioned between ethyl acetate and water, and the organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by flash chromatography on silica gel (methanol-dichloromethane) to give a residue containing 4-(2-benzylaminoethylamino)-8-(2,6-dichlorobenzoylamino)quinoline. A mixture of the obtained residue, 1,1'-carbonyldiimidazole (221 mg) and 1,8-diazabicyclo[5.4.0]undec-7-ene (191 mg) in dimethylformamide was stirred for 4 hours at ambient temperature and for 2 hours at 130° C. The mixture was partitioned between ethyl acetate and water, and the organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by flash chromatography on silica gel (methanol-dichloromethane) to give 4-(3-benzyl-2-oxoimidazolidin-1-yl)-8-(2,6-dichlorobenzoylamino)quinoline (150 mg).

Provenance & Evidence