Sodium Iodide → N-(2-fluoro-5-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)-9-(4-(trifluoromethoxy)phenyl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[1,5-a]azepin-2-amine

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Reaction Steps

A solution of 5-(5-chloro-1-(4-(trifluoromethoxy)phenyl)pentyl)-N-(2-fluoro-5-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)-1H-1,2,4-triazol-3-amine (820 mg, 1.480 mmol), sodium iodide (1.11 g, 7.40 mmol), and diisoproplylethylamine (0.256 mL, 1.48 mmol) in acetone (10 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 420 mg (52% yield) of the titled compound as an off-white solid. LC-MS (M+H)+ 518.3. 1H NMR (500 MHz, CHLOROFORM-4) δ ppm 8.55 (s, 1 H), 8.09 (d, J=7.6 Hz, 1 H), 7.48 (d, J=11.6 Hz, 1 H), 7.19-7.26 (m, 4 H), 6.83 (d, J=3.4 Hz, 1 H), 4.18-4.35 (m, 3 H), 3.81 (s, 3 H), 2.47 (s, 3 H), 2.16-2.24 (m, 1 H), 1.96-2.15 (m, 3 H), 1.80-1.95 (m, 2 H).

Provenance & Evidence