Hydrazine → N-(5-(5-chloro-1-(4-fluorophenyl)pentyl)-1H-1,2,4-triazol-3-yl)-6-(4-chloro-1H-imidazol-1-yl)-5-methoxypyridin-3-amine

Participants

Reaction Steps

Methyl 6-(4-chloro-1H-imidazol-1-yl)-5-methoxypyridin-3-ylcarbamimidothioate, hydroiodide (1.00 g, 2.349 mmol, from preparation O) and 6-chloro-2-(4-fluorophenyl)hexanoic acid (0.632 g, 2.58 mmol, from preparation AH) were coupled and then reacted with hydrazine (0.295 mL, 9.40 mmol) using a procedure analogous to Step A of Example 13. The crude product was purified using silica gel column chromatography (10-50, EtOAc/chloroform, linear gradient) to afford N-(5-(5-chloro-1-(4-fluorophenyl)pentyl)-1H-1,2,4-triazol-3-yl)-6-(4-chloro-1H-imidazol-1-yl)-5-methoxypyridin-3-amine (550 mg, 1.122 mmol, 47.7% yield). LC-MS (M+H)+ 490.2. After purification the product was still contaminated with a significant portion of HOBt. The impure product was used for subsequent chemistry without further purification.

Provenance & Evidence