Sodium Bicarbonate → 5-(5-Chlorobenzoxazol-2-yl)-2-methyl-1-(3,3,3-trifluoropropyl)benzimidazole

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To a solution of 5-chloro-2-(2-(3,3,3-trifluoropropyl)aminoanilin-5-yl)benzoxazole (see Working Example 138-1) (200 mg, 0.562 mmol) in ethanol (5 mL) was added ethyl acetimidate hydrochloride (104 mg, 0.843 mmol), and this was heated to reflux for 5 hours. After the reaction was complete, saturated aqueous sodium hydrogen carbonate solution was added, and this was extracted with chloroform. The organic layer obtained was dried over anhydrous sodium sulfate, filtered, and concentrated to give crude crystals that were washed with diethyl ether to yield the title compound (170 mg, 80% yield) as light green crystals.

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