1,3-Cyclohexanedione → HCID 178470344, compound

Participants

Reaction Steps

A suspension of 148.5 mg (0.96 mmol) of 3-amino-2-ethoxycarbonylpyrrole and 269.9 mg (0.96 mmol) of 5-(6,7-difluoro-1H-benzimidazol-2-ylsulfanyl)-furan-2-carbaldehyde (obtained from step 2) in 10 mL of n-butanol under argon is stirred at room temperature for 20 minutes. 1,3-Cyclohexanedione (108.0 mg, 0.96 mmol) is then added and the reaction mixture is heated at reflux temperature for 2 h. The mixture is then cooled to room temperature and concentrated under reduced pressure. The residue is taken up in ethanol, cooled to 0° C., triturated, filtered and washed 3 times with ethanol. 127 mg of 9-[5-(6,7-difluoro-1H-benzimidazol-2-ylsulfanyl)-furan-2-yl]-8-oxo-4,5,6,7,8,9-hexahydro-2H-pyrrolo[3,4-b]quinoline-3-carboxylic acid ethyl ester are obtained as a light-yellow crystalline powder. mp: 144-148° C. LCMS-DAD-ELSD: 509(−): [M−H]−; 511 (+): [M+H]+.

Provenance & Evidence