Methanesulfonyl chloride → N-[6-(4-Fluorobenzyl)-4-methoxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridin-1-yl]methanesulfonamide

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Reaction Steps

To a solution of 5-amino-2-(4-fluorobenzyl)-8-methoxy-3,4-dihydro-2,6-naphthyridin-1(2H)-one (0.889 g, 2.95 mmol) in pyridine (5 mL) was added dropwise methanesulfonyl chloride (0.575 g, 5.016 mmol). After stirring for an hour at room temperature, the product mixture was quenched with pH 7 buffer, then concentrated under vacuum. The residue was dissolved in CHCl3 and pH 7 buffer, the pH of the aqueous layer was adjusted to pH 5 with 1N NaOH and the layers separated. Several more extractions with CHCl3 were performed. The organic extracts were dried with Na2SO4, filtered, and concentrated under vacuum, then dissolved in toluene and CHCl3 and evaporated to provide the title compound.

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