1,2-Dichloroethane → HCID 178509905, Verbindung

Beteiligte Stoffe

Reaktionsschritte

EDC (0.025 g, 0.131 mmol) and HOBT (0.018 g, 0.131 mmol) were added to a solution of 3-{[3-(aminomethyl)-6-bromo-2-fluorophenyl]oxy}-5-chlorobenzonitrile (0.042 g, 0.119 mmol) and 4-chloro-2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxylic acid (0.050 g, 0.119 mmol) in DMF (2 mL). The mixture was stirred at RT for 4 hrs, saturated sodium bicarbonate was added and the solution was extracted with EtOAc. The organic layer was dried over sodium sulfate and concentrated. The crude product was dissolved in dichloromethane (2 mL) and trifluoroacetic acid (0.3 mL, 3.89 mmol) was added. The mixture was stirred at RT overnight. The solvent was evaporated and the residue was purified by reverse phase HPLC (acetonitrile:water with 0.1% formic acid) to give the title compound (0.030 g, 47%) as a white powder. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.99 (br. s., 1H), 8.32-8.41 (m, 1H), 7.79-7.84 (m, 1H), 7.57-7.65 (m, 1H), 7.47-7.52 (m, 1H), 7.44 (t, 1H), 7.31 (t, 1H), 5.54 (br. s., 1H), 4.45-4.53 (m, 2H), 4.37-4.44 (m, 2H). ES MS: m/z 512, 514.

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