1,2-Dichloroethane → HCID 178503457, compound

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Reaction Steps

To a solution of 4-(2-methylsulfanyl-pyrimidin-4-yloxy)-benzene-1,2-diamine (Example 18, Step B, 400 mg, 1.6 mmol, 1.0 eq.) in anhydrous CH3CN (20 mL) was added drop wise a solution of 1-chloro-4-isothiocyanato-2-trifluoromethylbenzene (380 mg, 1.6 mmol, 1.0 eq.) in anhydrous CH3CN (10 mL). The solution was stirred for 16 h at RT. EDC (470 mg, 2.4 mmol, 1.5 eq.) was added and the reaction was heated to 80° C. and stirred for 2 h. The solvent was removed under reduced pressure. The residue was dissolved in CH2Cl2, and the solution was washed with H2O (25 mL), NaHCO3 (aq., 25 mL) and brine (25 mL). The aqueous layers were back extracted with CH2Cl2 and the combined organic layers were dried over MgSO4, filtered and concentrated. The crude was further purified by column chromatography (0-100% EtOAc/hexanes) to yield (4-chloro-3-trifluoromethyl-phenyl)-[5-(2-methylsulfanyl-pyrimidin-4-yloxy)-1H-benzimidazol-2-yl]-amine. MS m/z=452.1 (M+H)+; MW Calc'd for C19H13ClF3N5OS: 451.86.

Provenance & Evidence