F[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][C:13]=2[F:20])[C:3]=1[CH:21]=O.O.[NH2:24][NH2:25]>COCCOC>[F:20][C:13]1[CH:14]=[C:15]([S:18][CH3:19])[CH:16]=[CH:17][C:12]=1[NH:11][C:4]1[C:5]([C:6]([OH:8])=[O:7])=[CH:9][CH:10]=[C:2]2[C:3]=1[CH:21]=[N:24][NH:25]2To a suspension of 4-fluoro-2-(2-fluoro-4-methylsulfanyl-phenylamino)-3-formyl-benzoic acid (105 mg, 0.32 mmol) in DME (5 mL) was added hydrazine hydrate (5 mL) and the reaction mixture heated at 90° C. for 18 hours. The volatile solvent was removed in vacuo and the residue acidified with concentrated HCl whilst applying cooling. The resultant precipitate was collected by filtration and washed with water to give the title compound as a tan solid (85 mg, 82%). LCMS (Method B) RT 3.12 [M+H]+ 318.
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