CS(C)=O.C(Cl)(=O)C(Cl)=O.[Cl:11][C:12]1[C:13]([N:18]2[CH2:23][CH2:22][CH:21]([OH:24])[CH2:20][CH2:19]2)=[N:14][CH:15]=[CH:16][CH:17]=1.C(N(CC)CC)C>C(Cl)Cl.O>[Cl:11][C:12]1[C:13]([N:18]2[CH2:23][CH2:22][C:21](=[O:24])[CH2:20][CH2:19]2)=[N:14][CH:15]=[CH:16][CH:17]=1At −78° C., DMSO (10 g, 138 mmol) was added slowly into a dichloromethane (40 ml) solution of oxalyl dichloride. After 15 minutes, N-(3-chloro-2-pyridyl)-4-hydroxy piperidine (compound 20) in methylene chloride was added dropwise into the reaction mixture. After 30 minutes, 31 g of triethylamine was slowly added, when the reaction solution was maintained at −78° C. Reaction mixture was slowly warmed to room temperature. Three times of water was added into the reaction solution. The reaction mixture was extracted by ethyl acetate. The organic layer was evaporated to give a crude product, which was purified using column chromatography to give the product. (13 g, 93%)
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