Ammonium formate → HCID 25166502, compound

Participants

Reaction Steps

Ammonium formate (350 mg, 5.5 mmol) was added to a stirred solution of 2′-Benzyloxy-biphenyl-4-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide (prepared by the method as described above) (156 mg, 0.26 mmol) in a mixture of MeOH (10 mL) and water (2 ml). 10% Pd/c (40 mg) was then added and the resulting mixture stirred at room temperature under an inert atmosphere. The reaction mixture was then stirred at reflux temperature for 3 hrs. The mixture was filtered over a bed of celite. The celite was washed with MeOH and the filtrate was concentrated. The residue was dissolved in EtOAc, washed with 5% aqueous NaOH solution, followed by saturated brine solution. The organic layer was dried over Na2SO4 and concentrated to get the residue. The residue was purified by preparative HPLC to afford 62 mg (47% yield) of 2′-Hydroxy-biphenyl-4-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide. LCMS Purity: 98.83%. 1H NMR (DMSO-d6): δ 9.6 (s, 1H), 8.64-8.5 (bs, 1H), 7.92-7.72 (m, 4H), 7.72-7.5 (m, 4H), 7.26-7.12 (d, 1H), 7.24-7.16 (t, 1H), 7.0-6.84 (m, 2H), 4.24-4.06 (bd, 2H), 3.82-3.52 (m, 4H), 3.52-3.42 (bs, 2H), 3.24-3.02 (bd, 2H).

Provenance & Evidence