Pyridine → 3-[2-(1-tert-Butoxycarbonylpiperidin-4-yloxy)-4-(methylthio)benzoylamino]-N-(5-chloropyridin-2-yl)pyridine-2-carboxamide

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Reaction Steps

The 2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-(methylthio)benzoic acid (201 mg, 0.55 mmol) was diluted with dichloromethane (5 mL), pyridine (52 μL, 0.64 mmol), and DMF (2 drops). Oxalyl chloride (52 μL, 0.60 mmol) was added and vigorous bubbling occurred. After about 30 minutes, the reaction was concentrated in vacuo. The residue was diluted with dichloromethane (5 mL) and the 3-amino-N-(5-chloropyridin-2-yl)pyridine-2-carboxamide (123 mg, 0.50 mmol) was added, followed by pyridine (72 μL, 0.64 mmol). The reaction was stirred overnight and then diluted with dichloromethane (50 mL) and washed with water (3×5 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated. The crude residue was purified by flash column chromatography (CH2Cl2 through 5% EtOAc/CH2Cl2) to give the desired product as a pale yellow amorphous solid (214 mg, 0.36 mmol, 72%).

Provenance & Evidence