Triethylamine → HCID 67357288, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 4-[4-(4-carboxyphenyl)-piperazin-1-yl]-benzoic acid tert-butyl ester (100 mg, 0.26 mmol) in methylene chloride (5 mL) was added oxalyl chloride (2M, 0.2 mL) and a catalytic amount of DMF. The mixture was stirred for 30 minutes and solvents were evaporated. The residue was dried and then mixed with 2-fluoro-5-trifluoromethylaniline (65 mg, 0.36 mmol) and triethyl amine (56 μL, 0.38 mmol) in toluene (6 mL). The mixture was heated in a sealed tube at 140° C. for 3 hrs. Solvents were then evaporated and the residue was extracted with water and ethyl acetate. The organic layer was dried and evaporated. The residue was triturated with ethyl acetate to give the intermediate 4-{4-[4-(2-chloro-5-trifluoromethyl-phenylcarbamoyl)-phenyl]-piperazin-1-yl}-benzoic acid tert-butyl ester. This intermediate was then suspended in methylene chloride (3 mL and trifluoro acetic acid (1 mL) was added. The mixture was stirred for 1 hr and solvents were evaporated. The residue was dried and then triturated with ethyl acetate to give 4-{4-[4-(2-fluoro-5-trifluoromethyl-phenylcarbamoyl)-phenyl]-piperazin-1-yl}-benzoic acid. LCMS calc for C25H21F4N3O3 (m/e) 487, obsd 488 (M+H).

Provenance & Evidence