[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.[Cl-].[NH4+].C([N:15]=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(=O)([O-])O.[Na+]>CN(C)C=O>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH2:15])=[O:10])=[N:6][CH:7]=1To a solution of 5-aminopyridine-2-carboxylic acid (2.0 g) in N,N-dimethylformamide (50 mL) were added ammonium chloride (3.9 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (5.1 mL) and 1-hydroxybenzotriazole (4.4 g), and the mixture was stirred overnight at room temperature. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate) to give the title compound (260 mg).
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