Sodium Iodide → N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-9-(2-fluorophenyl)-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-(2-fluorophenyl)pentyl)-N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-1H-1,2,4-triazol-3-amine (2.47 g, 5.05 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 (0-35% EtOAc/chloroform, linear gradient) to afford 234 mg (10% 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)+ 453.3. 1H NMR (500 MHz, chloroform-d) δ ppm 7.50 (d, J=1.53 Hz, 1 H) 7.44 (d, J=2.14 Hz, 1 H) 7.27-7.34 (m, 1 H) 7.21-7.26 (m, 1 H) 7.16 (t, J=7.17 Hz, 1 H) 7.04-7.13 (m, 2 H) 7.01 (d, J=1.53 Hz, 1 H) 6.76 (dd, J=8.39, 2.29 Hz, 1 H) 6.60 (s, 1 H) 4.38-4.48 (m, 2 H) 4.22 (dd, J=14.50, 9.92 Hz, 1 H) 3.74 (s, 3H) 2.00-2.27 (m, 4H) 1.79-1.94 (m, 2 H).

Provenance & Evidence