Hydrochloric Acid → HCID 178433214, compound

Participants

Reaction Steps

Add hydrochloric acid (10 mL, 40.0 mmol, 4 M in 1,4 dioxane) to tert-butyl N-[[6-(difluoromethyl)-5-[[4-methyl-5-[4-(trifluoromethyl)phenyl]-1H-imidazol-2-yl]carbamoyl]-3-pyridyl]methyl]carbamate (0.212 g, 0.403 mmol) and stir overnight. Dilute with water, and extract with Et2O. Adjust the pH to ˜8 with a saturated sodium bicarbonate aqueous solution. Extract with EtOAc (3×30 mL). Dry the organic extracts over sodium sulfate; filter; collect the filtrate; and concentrate the filtrate under reduced pressure. Purify by reverse phase flash chromatography (Analogix® 40 g @ 40 mL/min) eluting with a gradient of 2-55% ACN/water over 30 minutes. Concentrate the appropriate fractions under reduced pressure until all the ACN is removed and only water remains. Add a saturated sodium bicarbonate aqueous solution (30 mL), and extract with EtOAc (3×20 mL). Dry the organic extracts over sodium sulfate; filter; collect the filtrate; and concentrate the filtrate under reduced pressure to give the title compound as a light yellow solid (0.098 g, 57% yield). 1H NMR (400.43 MHz, d6-DMSO) δ 8.71-8.69 (m, 1H), 8.16 (s, 1H), 7.79-7.77 (m, 2H), 7.69-7.67 (m, 2H), 7.42-7.28 (m, 1H), 3.81 (s, 2H), 2.43 (s, 3H).

Provenance & Evidence