Dimethyl Sulfoxide → HCID 10299623, compound

Participants

Reaction Conditions

Reaction Steps

A solution of dimethyl sulfoxide (30 mg) in methylene chloride (1 ml) was added to a solution of oxalyl chloride (37 mg) in methylene chloride (4 ml) at −78° C. under a nitrogen atmosphere. After stirring at the same temperature for 1 hour, a solution of the compound obtained in Example 13 (70 mg) in methylene chloride (4 ml) was added thereto and then the stirring was continued at −78° C. for 1 hour. The reaction temperature was raised to at −30° C. and, after stirring at 30 minutes, triethylamine (150 μl) was added thereto and then the solution temperature was slowly raised to at 0° C. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and then evaporated under reduced pressure to remove the solvent. The residue was subjected to column chromatography on silica gel to obtain 1-{[3-chloro-4-(4-methoxyphenyl)-6,6-dimethyl-7-oxo-5,6,7,8-tetrahydro [1]benzothieno[2,3-b]pyridin-2-yl]methyl}-2,5-pyrrolidinedione:

Provenance & Evidence