1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-(3-Acetylaminophenyl)-5-(5-chlorobenzoxazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazole

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To a solution of 5-chloro-2-(2-(tetrahydropyran-4-yl)aminoanilin-5-yl)benzoxazole (see Working Example 100-2) (250 mg, 0.727 mmol) in dimethylformamide (5 mL) was added 3-acetamidobenzoic acid (130 mg, 0.727 mmol) and WSC (167 mg, 0.872 mmol), and this was stirred at room temperature for 23 hours. Saturated aqueous sodium hydrogen carbonate solution was added, the precipitated crystals were filtered, washed with water and then dried. To a solution of the residue obtained in dioxane (5 mL) was added methanesulfonic acid (2 drops), and this was heated to reflux for 3 hours. After the reaction was complete, saturated aqueous sodium hydrogen carbonate solution was added, the precipitated crystals were filtered, washed with water and then dried. The residue obtained was purified by silica gel column chromatography to yield the title compound (50.5 mg, 14%) as white crystals.

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