Trifluoroacetic acid → HCID 66740735, 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 (50 mg, 93.6 μmol) and (S)-4-t-butoxy-2-(t-butoxycarbonylamino)-4-oxobutanoic acid (2.4 equiv, 66 mg, 0.244 mmol) in DCM (3 mL) was added HATU (2.2 equiv, 80 mg, 0.204 mmol) followed by DIPEA (3.0 equiv, 49 mL, 0.281 mmol). The mixture was stirred at room temperature overnight. Purification by column chromatography provided the protected product. Deprotection was performed by stirring with TFA (1 mL) and DCM (1 mL) for 1 h. Purification by HPLC using NH4CO3 as a modifier afforded the title compound as a white solid (11 mg, 18%). 1H NMR (400 MHz, MeOD) δ 7.43 (s, 1H), 7.37 (d, J=11.6 Hz, 1H), 7.25 (s, 1H), 7.18 (d, J=8.4 Hz, 1H), 6.80 (m, 2H), 6.56-6.49 (m, 2H), 6.38-6.30 (m, 1H), 6.22 (m, 1H), 4.19 (t, J=7.6, 1H), 4.00 (dd, J=13.5, 7.4 Hz, 2H), 3.71 (s, 3H), 2.89-2.78 (m, 1H), 2.67 (dd, J=17.0, 8.1 Hz, 1H), 1.54 (s, 3H), 1.53 (s, 3H); MS (EI) m/z 649 (MH+).

Provenance & Evidence