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【结 构 式】 
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【药物名称】Itameline, RU-47213 【化学名称】(E)-1-(4-Chlorophenoxycarbonyl)-1,2,5,6-tetrahydropyridine-3-carboxaldehyde O-methyloxime 【CA登记号】121750-57-0 【 分 子 式 】C14H15ClN2O3 【 分 子 量 】294.74025 |
【开发单位】Aventis Pharma (Originator) 【药理作用】Cognition Disorders, Treatment of, NEUROLOGIC DRUGS, Muscarinic M1 Agonists |
合成路线1
Pyridine-3-carboxaldehyde O-methyloxime (I) is prepared either by methylation of 3-pyridinealdoxime sodium salt or by condensation of 3-pyridinecarboxaldehyde with methoxylamine in water. Quaternization of (I) with ethyl iodide gives 3-(methoxyiminomethyl)-1-ethylpyridinium iodide (II), which is reduced by means of sodium borohydride in methanol to 1-ethyl-1,2,5,6-tetrahydropyridine-3-carboxaldehyde O-methyloxime (III). Cleavage of the ethyl group is obtained by reaction with 4-chlorophenylchloroformate in refluxing dichloroethane to yield RU 47213. Ru 47213 is obtained as pure (E)-isomer. Under UV irradiation in toluene it is partially converted into the sterically unfavored (Z)-isomer.
| 【1】 Barzaghi, F.; Galliani, G.; Toja, E.; RU 47213. Drugs Fut 1994, 19, 5, 454. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 12849 | Nicotinaldehyde; 3-Pyridinecarboxaldehyde | 500-22-1 | C6H5NO | 详情 | 详情 |
| (D) | 16170 | 1,2-dichloroethane | 107-06-2 | C2H4Cl2 | 详情 | 详情 |
| (B) | 31260 | nicotinaldehyde oxime | 1193-92-6 | C6H6N2O | 详情 | 详情 |
| (I) | 12850 | Nicotinaldehyde O-methyloxime | C7H8N2O | 详情 | 详情 | |
| (II) | 31259 | 1-ethyl-3-[(methoxyimino)methyl]pyridinium iodide | C9H13IN2O | 详情 | 详情 | |
| (III) | 31261 | 1-ethyl-1,2,5,6-tetrahydro-3-pyridinecarbaldehyde O-methyloxime | C9H16N2O | 详情 | 详情 | |
| (C) | 17779 | 1-chloro-4-[(chlorocarbonyl)oxy]benzene | 7693-45-0 | C7H4Cl2O2 | 详情 | 详情 |