Sodium Iodide → HCID 58109981, compound

Participants

Reaction Steps

A solution of 5-(5-chloro-1-(4-(trifluoromethoxy)phenyl)pentyl)-N-(3-fluoro-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)-1H-1,2,4-triazol-3-amine (3.07 g, 5.85 mmol), sodium iodide (4.38 g, 29.3 mmol), and diisoproplylethylamine (5.11 mL, 29.3 mmol) in acetone (100 mL) was heated in a sealed vessel at 100° C. for 12 h. The reaction was concentrated in vacuo. Water (250 mL) was added and the mixture was extracted with EtOAc (2×250 mL). The combined organic layers were washed with brine (50 mL), dried (MgSO4), filtered, and concentrated in vacuo. Ethanol (50 mL) was added to the residue. The mixture was stirred at rt for 30 min. The solid was collected by vacuum filtration to afford 630 mg (21% yield) of the titled compound as an off-white solid. LC-MS (M+H)+ 488.5. 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 8.39 (d, J=2.4 Hz, 1 H), 7.68 (dd, J=14.0, 2.4 Hz, 1 H), 7.61 (t, J=8.5 Hz, 1 H), 7.17-7.26 (m, 4H), 7.02 (dd, J=89, 2.4 Hz, 1 H), 6.78 (s, 1H), 4.31 (dd, J=8.5, 2.4 Hz, 1 H), 4.26 (t, J=4.9 Hz, 2 H), 2.50 (s, 3 H), 2.17-2.29 (m, 1H), 2.06-2.16 (m, 1H), 1.86-2.03 (m, 4H).

Provenance & Evidence