Hydrazine → HCID 178505667, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (S,Z)-methyl N′-benzoyl-N-(1-(3-fluoro-5-(trifluoromethyl)phenyl)-1-(4-fluorophenyl)-2-phenylethyl)carbamimidothioate (58 mg, 0.1 mmol) and TEA (28 μL, 0.2 mmol) in CH3CN (1 mL) was added drop wise a solution of AgNO3 (26 mg, 0.15 mmol) in CH3CN (1 mL), followed by the addition of NH2NH2 (10 μL, 0.1 mmol). The reaction mixture was heated at 60° C. for 1 h and allowed to cool to room temperature. The solid was removed by filtration and the filtrate was concentrated. The residue was purified by ISCO chromatography (4 g column) using hexanes/EtOAc (0-30%) over 10 min to give (S)-N-(1-(3-fluoro-5-(trifluoromethyl)phenyl)-1-(4-fluorophenyl)-2-phenylethyl)-5-phenyl-4H-1,2,4-triazol-3-amine as a white solid (36 mg, 69% yield). LCMS: RT=4.25 min [M+H] 520.97 (Phenomenex Luna C18 column, 4.6×50 mm eluting with 10-90% MeOH/H2O over 4 minutes containing 0.1% TFA; 4 mL/min, monitoring at 220 nm). NMR: 400 MHz 1H (CDCl3) 7.77 ppm, 2H, dd, J=7.83, 1.52 Hz; 7.37 ppm, 4H, m; 7.26 ppm, 4H, m; 7.10 ppm, 3H, m; 6.98 ppm, 2H, m; 6.63 ppm, 2H, d, J=7.33 Hz; 3.97 ppm, 1H, m; 3.85 ppm, 1H, m.

Provenance & Evidence