Benzene → HCID 19787184, compound

Participants

Reaction Steps

To a mixture of 4-(2-chlorophenyl)-6,7-dihydro-2 -ethyl-7-methyl-6-oxothieno[2,3-b]pyridine-5-carboxylic acid (347 mg), diphenylphosphoryl azide (330 mg) and benzene (4 ml) was added dropwise triethylamine (0.14 ml). The mixture was stirred at room temperature for 30 minutes, stirred under reflux for 30 minutes and then 2,4-difluoroaniline (0.12 ml) was added. The mixture was refluxed for 4 hours, washed with water, dried over MgSO4, and then the solvent was distilled off. The residue was chromatographed on a silica gel and eluted with chloroform/ethyl acetate/metanol (9:1:0.25). The solvent was distilled off to obtain N-[4-(2-chlorophenyl)-6,7-dihydro-2-ethyl-7-methyl-6-oxothieno[2,3-b]pyridin-5-yl]-N'-(2,4-difluorophenyl)urea as colorless powder (210 mg, 44.4%).

Provenance & Evidence