Acetic Anhydride → HCID 178474546, compound

Participants

Reaction Steps

Pyridonyl guanidine compound (Z)-N-(((3-chloro-4-fluorobenzyl)amino)((6-hydroxypyridin-2-yl)amino)methylene)-4-(trifluoromethyl)benzamide was prepared based on the procedures described in Example 1. Then, (Z)-N-(((3-chloro-4-fluorobenzyl)amino)((6-hydroxypyridin-2-yl)amino)methylene)-4-(trifluoromethyl)benzamide (0.1 g, 0.214 mmol) was dissolved in pyridine (1 mL) with 4-dimethylaminopyridine (0.026 g, 0.214 mmol) under nitrogen at room temperature and acetic anhydride was added (0.022 g, 0.214 mmol). The reaction mixture was stirred at room temperature for 4 h forming a thick white slurry. Analysis by RP-HPLC indicated a ˜1:1 mixture of starting material and product. Additional pyridine (approximately 0.5 mL) and acetic anhydride (˜10 uL) were added. Stirring was continued for another 4 h then the mixture was diluted with water and ethyl acetate. Saturated aqueous NH4Cl was added to the mixture and the layers were separated. The organic layer was washed with water then brine and dried (MgSO4). Chromatography, eluting with 30-50% ethyl acetate in hexanes, gave a white solid which was triturated with diethyl ether to provide (E)-N-((N-(3-chloro-4-fluorobenzyl)acetamido)((6-hydroxypyridin-2-yl)amino)methylene)-4-(trifluoromethyl)benzamide (52 mg, 48%).

Provenance & Evidence