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【结 构 式】 
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【药物名称】 【化学名称】2-[2-(4-Methoxy-3,5-dimethylpyridin-2-yl)ethyl-2-methyl-5-(trifluoromethyl)-2,3-dihydrobenzothiazole 【CA登记号】212779-16-3 【 分 子 式 】C19H21F3N2OS 【 分 子 量 】382.45122 |
【开发单位】Il-Yang (Originator) 【药理作用】Antiulcer Drugs, Gastric Antisecretory Drugs, GASTROINTESTINAL DRUGS, H+/K+-ATPase Inhibitors |
合成路线1
Reaction of chloromethylpyridine (I) with NaOH in aqueous THF afforded alcohol (II), which was oxidized to formylpyridine (III) with selenium dioxide in refluxing pyridine. Subsequent condensation of aldehyde (III) with phosphorane (IV) in THF provided enone (V), and this was hydrogenated in the presence of Pd/C in MeOH to give (VI). Finally, condensation of ketone (VI) with aminothiophenol (VII) in the presence of p-toluenesulfonic acid in refluxing benzene yielded the corresponding benzothiazolidine.
| 【1】 Yoon, S.-H.; Seo, S.; Lee, Y.; Hwang, S.; Kim, D.Y.; Syntheses of 2-[(3,5-dimethyl-4-methoxypyridyl)alkyl]benzothiazolidine derivatives as a potential gstric H+/K+-ATPase inhibitor. Bioorg Med Chem Lett 1998, 8, 14, 1909. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 16521 | 2-(chloromethyl)-3,5-dimethyl-4-pyridinyl methyl ether; 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine; 2-Chloromethyl-3,5-dimethyl-4-methoxypyridine | 86604-75-3 | C9H12ClNO | 详情 | 详情 |
| (II) | 18785 | (4-methoxy-3,5-dimethyl-2-pyridinyl)methanol | C9H13NO2 | 详情 | 详情 | |
| (III) | 18786 | 4-methoxy-3,5-dimethyl-2-pyridinecarbaldehyde | C9H11NO2 | 详情 | 详情 | |
| (IV) | 18787 | 1-(triphenylphosphoranylidene)acetone | 1439-36-7 | C21H19OP | 详情 | 详情 |
| (V) | 18788 | (E)-4-(4-methoxy-3,5-dimethyl-2-pyridinyl)-3-buten-2-one | C12H15NO2 | 详情 | 详情 | |
| (VI) | 18789 | 4-(4-methoxy-3,5-dimethyl-2-pyridinyl)-2-butanone | C12H17NO2 | 详情 | 详情 | |
| (VII) | 12097 | 2-Amino-4-(trifluoromethyl)benzenethiol; 2-Amino-4-(trifluoromethyl)phenylhydrosulfide | C7H6F3NS | 详情 | 详情 |