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

Participants

Reaction Steps

Methyl 3-fluoro-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenylcarbamimidothioate, hydroiodide (0.750 g, 1.91 mmol, from preparation Q) and 6-chloro-2-(4-(2,2,2-trifluoroethoxy)phenyl)hexanoic acid (0.650 g, 2.00 mmol, from preparation AW) were coupled [N-methylmorpholine (1.05 mL, 9.54 mmol) was substituted for N,N-diisopropylethylamine] and then reacted with hydrazine (0.300 mL, 9.54 mmol) using a procedure analogous to Step A of Example 13. After an aqueous workup, 5-(5-chloro-1-(4-(2,2,2-trifluoroethoxy)phenyl)pentyl)-N-(5-fluoro-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)+ 538.5.

Provenance & Evidence