O=[C:2]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[C:10]([O:12]CC)=O.[NH2:15][C:16]1[CH:17]=[C:18]([CH:23]=[CH:24][N:25]=1)[C:19]([O:21][CH3:22])=[O:20].C(=O)([O-])[O-].[Na+].[Na+]>ClCCCl>[CH3:22][O:21][C:19]([C:18]1[CH:23]=[CH:24][N:25]2[C:10](=[O:12])[C:3]3[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:2]=3[N:15]=[C:16]2[CH:17]=1)=[O:20]A solution of ethyl 2-oxocyclooctanecarboxylate (1 g, 5.05 mmol) and methyl 2-aminoisonicotinate (0.768 g, 5.05 mmol) in PPA (2.5 mL) and 1,2-dichloroethane (5 mL) was stirred at 85° C. for 18 hours. The reaction mixture was then cooled to ambient temperature. A chilled saturated sodium carbonate solution was added to adjust pH to 8. The resulting mixture was extracted with ethyl acetate (4×100 mL). The combined organic layers were washed with brine and dried over anhydrous sodium sulfate. After filtration and concentration, the crude product was purified by silica gel chromatography purification to afford 157 mg of desired product.
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