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

Participants

Reaction Steps

Methyl 3-fluoro-4-(5-methyl-1H-1,2,4-triazol-1-yl)phenylcarbamimidothioate, hydroiodide (1.50 g, 3.81 mmol, from preparation C) and 6-chloro-2-(4-(2,2,2-trifluoroethoxy)phenyl)hexanoic acid (1.30 g, 4.00 mmol, from preparation AW) were coupled [N-methylmorpholine (2.10 mL, 19.1 mmol) was substituted for N,N-diisopropylethylamine] and then reacted with hydrazine (0.598 mL, 19.1 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-(3-fluoro-4-(5-methyl-1H-1,2,4-triazol-1-yl)phenyl)-1H-1,2,4-triazol-3-amine (2.11 g, 3.92 mmol, quantitative yield) was obtained as a brown foamy solid. The crude product was used in the next step without purification. LC-MS (M+H)+ 538.4.

Provenance & Evidence