Ethanol → HCID 53354117, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 8-(3,4-difluorophenyl)-6-fluoro-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-amine (74 mg, 276 μmol), 1-(3-methyl-1,2,4-thiadiazol-5-yl)piperidin-4-one (82 mg, 414 μmol) and titanium(IV) isopropoxide (240 mg, 253 μL, 828 μmol) dissolved in dichloroethane (6 mL) was heated to 85° C. for 12 hours. Further 1-(3-methyl-1,2,4-thiadiazol-5-yl)piperidin-4-one (54 mg, 276 μmol) was added and stirred at 85° C. for another two hours. The reaction mixture was cooled to 50° C., sodium borohydride (41.7 mg, 1.1 mmol) and ethanol (3 mL) were added and stirred at 50° C. for one hour. The solvent was evaporated, the residue extracted with 2 N Na2CO3 solution and ethyl acetate. The organic layers were combined, dried over Na2SO4, filtered and the solvent was evaporated. The residue was purified by flash chromatography (silica gel, 70 g, 0% to 15% MeOH/NH4OH (9:1) in dichloromethane) and then by preparative HPLC. The title compound was obtained as light green foam (37.1 mg, 30%).

Provenance & Evidence