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

Participants

Reaction Steps

Methyl 2-fluoro-5-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenylcarbamimidothioate, hydroiodide (0.485 g, 1.642 mmol, from preparation B) and 6-chloro-2-(4-fluorophenyl)hexanoic acid (0.442 g, 1.806 mmol, from preparation AE) were coupled and then reacted with hydrazine (0.206 mL, 6.56 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-(2-fluoro-5-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)-1H-1,2,4-triazol-3-amine (97 mg, 0.20 mmol, 12% yield). LC-MS (M+H)+ 488.2.

Provenance & Evidence