C[O:2][C:3](=[O:22])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:21])[NH:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[CH:8][N:7]=1.[OH-].[Na+].Cl>C1COCC1>[F:20][C:17]1[CH:16]=[CH:15][C:14]([NH:13][C:12]([C:9]2[CH:10]=[CH:11][C:6]([O:5][CH2:4][C:3]([OH:22])=[O:2])=[N:7][CH:8]=2)=[O:21])=[CH:19][CH:18]=1To a solution of [5-(4-fluorophenylcarbamoyl)pyridin-2-yloxy]acetic acid methyl ester (0.052 g, 0.17 mmol) in THF (1.2 mL) was added an aqueous solution of sodium hydroxide (0.34 mL of a 1 M solution, 0.34 mmol). After 30 minutes the reaction was acidified to pH 3 with 6N HCl and the solvent removed in vacuo. The solids were washed with cold water and the volatiles removed to yield 0.43 g (82%) of the titled product as a white solid: 1H NMR (300 MHz, DMSO-d6) δ 10.29 (s, 1H), 8.67 (m, 1H), 8.20 (m, 1H), 7.71 (m, 2H), 7.17 (m, 2H), 7.00 (m, 1H), 4.88 (m, 2H); MS (EI) m/z 289.06 (M−H)−.
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