Trifluoroacetic acid → HCID 178489995, compound

Participants

Reaction Steps

To a solution of 3-chloro-4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-5-fluoroaniline (175 mg, 0.322 mmol) in CHCl3 (10 mL) was added triphosgene (97 mg, 0.322 mmol) followed by Et3N (227.6 mg, 2.254 mmol) at 0° C. The mixture was stirred at room temperature 20 min. PMC protected L-arginine was added to the reaction mixture and allowed to stir at the same temperature overnight. Purification by column chromatography provided the protected product. Deprotection was performed by stirring with TFA (2 mL) and DCM (2 mL) for 1 h. Purification on HPLC yielded the title compound (52 mg). 1H NMR (400 MHz, MeOD) δ 7.24 (s, 1H), 7.26-7.12 (m, 3H), 6.81 (d, J=8.7 Hz, H), 6.79 (d, J=8.7 Hz, 1H), 6.54-6.48 (m, 2H), 6.25-6.14 (m, 2H), 4.22 (t, J=5.7 Hz, 1H), 3.97 (s, 2H), 3.68 (s, 3H), 3.23 (dt, J=13.6, 6.7 Hz, 2H), 2.08-1.77 (m, 4H), 1.53 (s, 6H); MS (EI) m/z 734 (MH+).

Provenance & Evidence