Water → HCID 86721271, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-{2-[5-(4-fluorophenyl)-1H-pyrazol-4-yl]-1,3-thiazol-4-yl}-N-(tetrahydro-2H-pyran-4-ylmethyl)acetamide (58 mg, 0.14 mmol), (bromomethyl)cyclobutane (0.033 mL, 0.29 mmol) and potassium carbonate (40.0 mg, 0.29 mmol) in acetonitrile (3 mL) was stirred at 80° C. for 1 hr. To the reaction mixture were further added potassium carbonate (40.0 mg, 0.29 mmol) and (bromomethyl)cyclobutane (0.033 mL, 0.29 mmol), and the mixture was further stirred at 80° C. for 2 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by NH-silica gel column chromatography (solvent gradient; 30→90% ethyl acetate/hexane) to give a mixture (1:3 (mol/mol), 55 mg, 0.118 mmol, 84%) of the title compound and 2-(2-(1-(cyclobutylmethyl)-3-(4-fluorophenyl)-1H-pyrazol-4-yl)thiazol-4-yl)-N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide as a pale-yellow solid.

Provenance & Evidence