Hydrazine → 5-(5-chloro-1-(4-fluorophenyl)pentyl)-N-(3-fluoro-4-(5-methyl-1H-1,2,4-triazol-1-yl)phenyl)-1H-1,2,4-triazol-3-amine

Participants

Reaction Steps

Methyl 3-fluoro-4-(5-methyl-1H-1,2,4-triazol-1-yl)phenylcarbamimidothioate, hydroiodide (0.739 g, 2.79 mmol, from preparation C) and 6-chloro-2-(4-fluorophenyl)hexanoic acid (0.750 g, 3.07 mmol, from preparation AE) were coupled and then reacted with hydrazine (0.350 mL, 11.2 mmol) using a procedure analogous to Step A of Example 13. The crude products were purified using silica gel chromatography (0-95% ethyl acetate/chloroform) to afford 5-(5-chloro-1-(4-fluorophenyl)pentyl)-N-(3-fluoro-4-(5-methyl-1H-1,2,4-triazol-1-yl)phenyl)-1H-1,2,4-triazol-3-amine (230 mg, 0.502 mmol, 18% yield) as a viscous oil. LC-MS (M+H)+ 458.2.

Provenance & Evidence