4-Methylmorpholine → 5-(5-chloro-1-(4-(trifluoromethoxy)phenyl)pentyl)-N-(3-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 3-fluoro-5-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenylcarbamimidothioate, hydroiodide (0.575 g, 1.36 mmol, from preparation 5) and 6-chloro-2-(4-(trifluoromethoxy)phenyl)hexanoic acid (0.528 g, 1.70 mmol, from preparation AI) were coupled [N-methylmorpholine (0.747 mL, 6.79 mmol) was substituted for N,N-diisopropylethylamine] and then reacted with hydrazine (0.213 mL, 6.80 mmol) using a procedure analogous to Step A of Example 13. After an aqueous workup, 5-(5-chloro-1-(4-(trifluoromethoxy)phenyl)pentyl)-N-(3-fluoro-5-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)-1H-1,2,4-triazol-3-amine was obtained as a brown solid. The crude product was used in the next step without purification. LC-MS (M+H)+ 554.2.

Provenance & Evidence