Sodium Iodide → N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-9-(3,4,5-trifluorophenyl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[1,5-a]azepin-2-amine

Participants

Reaction Steps

A solution of 5-(5-chloro-1-(3,4,5-trifluorophenyl)pentyl)-N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-1H-1,2,4-triazol-3-amine (2.66 g, 5.06 mmol), sodium iodide (3.79 g, 25.3 mmol), and diisoproplylethylamine (1.77 mL, 10.1 mmol) in acetone (40 mL) was heated in a sealed vessel at 100° C. for 2 h. The reaction was concentrated in vacuo. The crude product was purified using silica gel column chromatography (35-50% EtOAc/chloroform, linear gradient) to afford 420 mg (17% yield) of the titled compound as a pale yellow solid. The solid was recrystallized from EtOH to afford an analytical sample. LC-MS (M+H)+ 489.2. 1H NMR (500 MHz, chloroform-d) δ ppm 7.52 (d, J=1.53 Hz, 1 H) 7.39 (d, J=2.14 Hz, 1H) 7.11 (d, J=8.55 Hz, 1 H) 7.03 (d, J=1.22 Hz, 1H) 6.79-6.92 (m, 3 H) 6.59 (s, 1 H) 4.24-4.35 (m, 1 H) 4.10-4.24 (m, 2 H) 3.82 (s, 3H) 1.94-2.20 (m, 4 H) 1.78-1.94 (m, 2 H).

Provenance & Evidence