Sodium Iodide → N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-9-(4-(2,2,2-trifluoroethoxy)phenyl)-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-(4-(2,2,2-trifluoroethoxy)phenyl)pentyl)-N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-1H-1,2,4-triazol-3-amine (2.02 g, 3.54 mmol), sodium iodide (2.65 g, 17.7 mmol), and diisoproplylethylamine (0.618 mL, 3.54 mmol) in acetone (25 mL) was heated in a sealed vessel at 100° C. for 4 h. The reaction was concentrated in vacuo. The crude product was purified using silica gel column chromatography (50% EtOAc/chloroform) to afford 281 mg (15% yield) of the titled compound as an off-white solid. LC-MS (M+H)+ 533.2. 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 7.51 (d, J=1.5 Hz, 1H), 7.41 (d, J=2.4 Hz, 1 H), 7.14 (m, J=8.9 Hz, 2 H), 7.09 (d, J=8.5 Hz, 1 H), 7.02 (d, J=1.5 Hz, 1 H), 6.95 (m, J=8.9 Hz, 2 H), 6.84 (dd, J=8.5, 2.1 Hz, 1 H), 6.66 (s, 1 H), 4.36 (q, J=8.1 Hz, 2 H), 4.20-4.27 (m, 3 H), 3.80 (s, 3 H), 2.16-2.29 (m, 1H), 2.05-2.13 (m, 1 H), 1.92-2.03 (m, 2 H), 1.83-1.90 (m, 2 H).

Provenance & Evidence