Triethylamine → Benzothiazole-6-carboxylic acid 4-(3-fluoro-benzyloxy)-benzylamide

Participants

Reaction Steps

To a solution of 4-(3-fluorobenzyloxy)-benzylamine described in Preparation Example 6 (129 mg, 0.558 mmol) and benzothiazole-6-carboxylic acid (100 mg, 0.558 mmol) in tetrahydrofuran (5 mL) were added benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (296 mg, 0.670 mmol) and triethylamine (93 μl, 0.670 mmol), and the solution was stirred overnight at room temperature. Ethyl acetate and water were added to the reaction solution, which was then partitioned, the organic layer was washed with water, and then, dried over anhydrous magnesium sulfate. The solvent was evaporated, the residue was purified by NH silica gel column chromatography (hexane:ethyl acetate), and the title compound (148 mg, 68%) was obtained as a white solid.

Provenance & Evidence