C[O-].[Na+].[CH3:4][N:5]([S:31]([CH3:34])(=[O:33])=[O:32])[C:6]1[N:15]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[C:13]([O:20]S(C2C=CC(C)=CC=2)(=O)=O)=[C:12]2[C:7]=1[CH:8]=[CH:9][CH:10]=[N:11]2.C(O)(=O)C>CO.CN(C=O)C>[OH:20][C:13]1[C:14]([C:16]([O:18][CH3:19])=[O:17])=[N:15][C:6]([N:5]([CH3:4])[S:31]([CH3:34])(=[O:33])=[O:32])=[C:7]2[C:12]=1[N:11]=[CH:10][CH:9]=[CH:8]2A solution of sodium methoxide (122 mg, 2.26 mmol) in dry methanol (5 mL) was added to methyl 5-[methyl(methylsulfonyl)amino]-8-{[(4-methylphenyl)sulfonyl]oxy}-1,6-naphthyridine-7-carboxylate (420 mg, 0.90 mmol) dissolved in a minimum amount of DMF and the resulting solution was heated to 50° C. for one hour. The reaction was cooled, glacial acetic acid (104 μL, 1.80 mmol) was added and the reaction was concentrated to dryness in vacuo. The resulting residue was triturated with ethanol and the solids were collected by vacuum filtration to give the desired product as a yellow solid.
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