[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N:12]([CH3:22])[S:13]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)(=[O:15])=[O:14])[N:11]=1)[C:5]([O:7]C)=[O:6].CO.[OH-].[Na+].Cl>CCOC(C)=O.C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N:12]([CH3:22])[S:13]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)(=[O:15])=[O:14])[N:11]=1)[C:5]([OH:7])=[O:6]
To a solution of methyl 2-chloro-6-[methyl(pyridin-3-ylsulfonyl)amino]isonicotinate (3.12 g, 9.13 mmol) in 1:1 MeOH:THF (60 mL total) was added 1N NaOH solution (27 mL, 27.4 mmol). After 1 h, reaction was concentrated in vacuo. Reaction was diluted with EtOAc (100 mL) and acidified with 1N HCl (50 mL) solution. The aqueous solution was extracted with EtOAc (100 mL×3). The combined organics were washed with brine (100 mL), dried over Mg2SO4, filtered, and concentrated in vacuo to give 2.63 g (88%) of 2-chloro-6-[methyl(pyridin-3-ylsulfonyl)amino]isonicotinic acid as a white solid. LC/MS [M+H]+=328.1.
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