Trifluoroacetic acid → HCID 178502061, compound

Participants

Reaction Steps

Methyl chloroformate (0.020 mL, 0.26 mmol) was added to a solution of 2-amino-4-chloro-N-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide (0.050 g, 0.086 mmol) and DIEA (0.075 mL, 0.43 mmol) in CH2Cl2 (0.5 mL). The reaction mixture was stirred at RT overnight. TFA (0.5 mL) was added and the reaction mixture was stirred at RT for another 1 h. The reaction mixture was then evaporated and taken up in MeOH (1 mL). NaBH4 (0.030 g, 0.80 mmol) was added and the reaction mixture was stirred overnight. CH2Cl2 and sat'd NaHCO3 were added and the solution was extracted with CH2Cl2. The organic layer was dried (Na2SO4), filtered, concentrated and purified by Reverse-Phase HPLC (water:acetonitrile with 0.1% TFA) to afford the title compound (0.008 g, 19%) as a white solid. 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.56 (s, 1H) 7.34-7.44 (m, 2H) 7.25-7.29 (m, 1H) 7.24 (s, 1H) 4.57-4.70 (m, 2H) 3.81 (s, 3H). ES-LCMS: m/z 512.01, 513.97 (M+1).

Provenance & Evidence