C([O:3][C:4]([C:6]1[C:11]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]#[CH:20])=[CH:15][C:14]=2[F:21])=[CH:10][C:9](=[O:22])[N:8]([CH3:23])[CH:7]=1)=[O:5])C.[OH-].[Na+]>CCO>[C:19]([C:16]1[CH:17]=[CH:18][C:13]([NH:12][C:11]2[C:6]([C:4]([OH:5])=[O:3])=[CH:7][N:8]([CH3:23])[C:9](=[O:22])[CH:10]=2)=[C:14]([F:21])[CH:15]=1)#[CH:20]4-(4-Ethynyl-2-fluoro-phenylamino)-1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester (0.67 mg, 2.13 mmol) was suspended in EtOH (20 mL), to which was added NaOH (0.26 g, 6.40 mmol). This mixture was stirred at 70° C. for 1 hour. The solvent was removed under reduced pressure. The residue was acidified with 1N HCl then the resulting precipitate was filtered and washed with water. The tan solid was dried under high vacuum pump to afford 4-(4-Ethynyl-2-fluoro-phenylamino)-1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (0.56 g, 91%). 1H NMR [(CD3)2SO, 400 MHz] δ 13.31 (v br s, 1H), 9.79 (s, 1H), 8.51 (s, 1H), 7.49 (dd, J=10.1, 1.9 Hz, 1H), 7.44 (dd, J=8.4, 1.7, 0.8 Hz, 1H), 7.32 (dd, J=8.5 Hz, 1H), 5.61 (dd, J=0.7 Hz, 1H), 4.25 (s, 1H), 3.41 (s, 3H). Anal. Calcd for C15H11FIN2O3: C, 62.94; H, 3.87; N, 9.79. Found: C, 62.56; H, 3.78; N, 9.30.
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