Taurine → HCID 86662221, compound

Participants

Reaction Steps

To a solution of 4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3-fluorobenzoic acid (50 mg, 0.095 mmol) in DCM (3 mL) was added thionyl chloride (14 μL, 0.19 mmol) at 0° C. After reluxing for 13 h, the reaction mixture was cooled to room temperature and concentrated in vacuo. The crude material was dissolved in DCM (3 mL). To this solution were added taurine (12.4 mg, 0.099 mmol) and Et3N (26 μL, 0.19 mmol). The mixture was stirred for 5 h at room temperature and concentrated in vacuo. The crude residue was triturated with EtOAc (10 mL), and filtered through Celite™. The filtrate was concentrated in vacuo and was purified by chromatography (silica, DCM-MeOH=10:1) to afford triethylammonium 2-(4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3-fluorobenzamido)ethanesulfonate (45 mg, 65%) as a white solid. 1H NMR (400 MHz, CD3OD): δ 7.54-7.47 (m, 2H), 7.27 (s, 1H), 7.15 (d, 1H), 7.06 (t, 1H) 6.81-6.77 (m, 2H), 6.48-6.45 (m, 2H), 6.06-6.03 (m, 2H), 4.04 (s, 2H), 3.85 (t, 2H), 3.69 (s, 3H), 3.24 (q, 6H), 3.13 (t, 2H), 1.50 (s, 6H), 1.33 (t, 9H); MS (EI) m/z 637 (MH+).

Provenance & Evidence