Dimethylformamide → 3-[2-acetoxy-4-methylthiobenzoylamino]-N-(5-chloropyridin-2-yl)pyridine-2-carboxamide

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Reaction Steps

To a 0° C. mixture of 2-acetoxy-4-methylthiobenzoic acid (5 g, 22.1 mmol), dichloromethane (75 mL), NEt3 (3.1 mL, 22.1 mmol) and DMF (17 μL, 0.221 mmol) was added oxalyl chloride (1.92 mL, 22.1 mL) at a rate to give gentle bubbling. The mixture was stirred for 1 h and then was concentrated in vacuo. The resulting residue was dissolved in dichloromethane (75 mL). To this solution was added 3-amino-N-(5-chloropyridin-2-yl)pyridine-2-carboxamide (5.5 g, 22.1 mmol) followed by NEt3 (3.1 mL, 22.1 mmol). The reaction mixture was stirred for 18 h, concentrated to a slurry in dichloromethane and chromatographed (75 g silica gel; 100% dichloromethane to 100% EtOAc) to give the title compound as an impure solid (8.5 g).

Provenance & Evidence