4-Methylmorpholine → 5-(5-chloro-1-(4-isopropoxyphenyl)pentyl)-N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-1H-1,2,4-triazol-3-amine

Participants

Reaction Steps

Methyl 4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenylcarbamimidothioate, hydroiodide (1.50 g, 3.53 mmol, from preparation A) and 6-chloro-2-(4-isopropoxyphenyl)hexanoic acid (1.26 g, 4.42 mmol, from preparation AV) were coupled [N-methylmorpholine (2.00 mL, 17.7 mmol) was substituted for N,N-diisopropylethylamine] and then reacted with hydrazine (0.556 mL, 17.7 mmol) using a procedure analogous to Step A of Example 13. The crude products were purified using silica gel chromatography (50% ethyl acetate/chloroform) to afford 5-(5-chloro-1-(4-isopropoxyphenyl)pentyl)-N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-1H-1,2,4-triazol-3-amine (805 mg, 1.52 mmol, 43% yield) as an off-white solid. LC-MS (M+H)+ 529.3.

Provenance & Evidence