p-Toluenesulfonic acid → HCID 66743201, compound

Participants

Reaction Steps

A mixture of 4-bromo-3-(methylamino)-5-(1H-pyrazol-4-yl)thiophene-2-carboxamide dihydrochloride (90 mg, 0.267 mmol), saturated aqueous NaHCO3 (50 mL) and EtOAc (50 mL) was shaken well. The organic layer was collected, dried over MgSO4, filtered and concentrated under reduced pressure. This residue was mixed with cyclohexanone (2.00 mL, 19.3 mmol), PTSA (93 mg, 0.491 mmol), MgSO4 (64.2 mg, 0.533 mmol) and DMF (2 mL). This mixture was stirred at 80° C. for 4 h. The mixture was poured into saturated aqueous NaHCO3 and extracted with 3:1 EtOAc/THF (100 mL), and the extract was dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (Purif, silica gel, 95:5 hexane/EtOAc to EtOAc) to afford a white solid. This solid was triturated with EtOAc, and the precipitate was collected by filtration to afford the title compound (46.2 mg, 46%) as a white solid:

Provenance & Evidence