Benzenesulfonamide → HCID 86752960, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-[5-(2-cyclopropyl-5,7-dimethylimidazo[4,5-b]pyridin-3-ylmethyl)thiophen-2-yl]cyclopenten-3-ene carboxylic acid (Example 3) (500 mg, 1.27 mmol) and 1,1-carbonyl diimidazole (250 mg, 1.27 mmol) in THF (25 ml) was heated under reflux for 3 hours, then a solution of benzenesulfonamide (242 mg, 1.6 mmol) and DBU (243 mg, 1.6 mmol) in THF (2.0 ml) was added. The reaction mixture was heated at 40° C. for 19 hours, cooled to 23° C. and concentrated in vacuo. The residue was dissolved in water and acidified with 10% aqueous NaH2PO3. The aqueous mixture was extracted with EtOAc (3×25 ml). The combined extracts were dried and concentrated in vacuo. The crude residue was chromatographed on SiO2 gel using 2% MeOH/EtOAc to give 406 mg of the title compound (60% yield).

Provenance & Evidence