[C:1]([C:4]1[C:9]([C:10]([OH:12])=[O:11])=[C:8]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:20])[C:7]([F:21])=[C:6]([F:22])[CH:5]=1)(=O)[CH3:2].Cl.[NH2:24]O>CO.O.CCOC(C)=O>[Cl:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[NH:13][C:8]1[C:9]2[C:10](=[O:11])[O:12][N:24]=[C:1]([CH3:2])[C:4]=2[CH:5]=[C:6]([F:22])[C:7]=1[F:21]To a solution of 6-acetyl-2-(2-chlorophenylamino)-3,4-difluorobenzoic acid (50 mg, 0.15 mmol) and hydroxylamine hydrochloride (11 mg, 0.15 mmol) in MeOH-H2O (1 mL/0.5 mL) was added TEA (0.022 mL, 0.15 mmol) at room temperature. The resulting mixture was stirred for 16 hours at room temperature. The reaction mixture was diluted with EtOAc and washed with water. The organic layer was dried over MgSO4, filtered and concentrated in vacuo to give the crude material that was purified by silica gel flash column chromatography (100% CH2Cl2) to afford the desired product (26.8 mg, 54%).
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