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【结 构 式】 
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【药物名称】Raclopride, A-40664(tartrate) 【化学名称】(S)-3,5-Dichloro-N-[(1-ethyl-2-pyrrolidinyl)methyl]-2-hydroxy-6-methoxybenzamide 【CA登记号】84225-95-6 【 分 子 式 】C15H20Cl2N2O3 【 分 子 量 】347.24425 |
【开发单位】AstraZeneca (Originator) 【药理作用】Antipsychotic Drugs, Nausea and Vomiting, Treatment of, NEUROLOGIC DRUGS, PSYCHOPHARMACOLOGIC DRUGS, Dopamine D2 Antagonists |
合成路线1
The reaction of 3,5-dichloro-6-methoxysaliclic acid (I) with refluxing SOCl2 gives the corresponding acyl chloride (II), which is condensed with 1-ethyl-2-(aminomethyl)pyrrolidine (III) in methylene chloride yielding the amide (IV). Finally, this compound is partially demethylated with BBr3 in methylene chloride ether.
| 【1】 de Paulis, T.; et al.; Potential neuroleptic agents. 4. Chemistry, behavioral pharmacology, and inhibition of [3H]spiperone binding of 3,5-disubstituted N-[(1-ethyl-2-pyrrolidinyl)methyl]-6-methoxysalicylamides. J Med Chem 1986, 29, 1, 61. |
| 【2】 Florvall, G.L.; Lundstroem, J.O.G.; Raemsby, S.I.; Oegren S.O. (AstraZeneca plc); Benzamido-derivatives. DD 201886; EP 0060235; JP 57159762; US 4789683 . |
| 【3】 Prous, J.; Castaner, J.; Raclopride. Drugs Fut 1986, 11, 5, 387. |
| 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) | 24010 | 3,5-Dichloro-6-methoxysaliclic acid; 3,5-Dichloro-2,6-dimethoxybenzoic acid | 73219-91-7 | C9H8Cl2O4 | 详情 | 详情 |
| (II) | 24011 | 3,5-dichloro-2,6-dimethoxybenzoyl chloride | C9H7Cl3O3 | 详情 | 详情 | |
| (III) | 21345 | (2S)-1-Ethyl-2-(aminomethyl)pyrrolidine; [(2S)-1-Ethylpyrrolidinyl]methanamine | C7H16N2 | 详情 | 详情 | |
| (IV) | 24013 | 3,5-dichloro-N-[[(2R)-1-ethylpyrrolidinyl]methyl]-2,6-dimethoxybenzamide | C16H22Cl2N2O3 | 详情 | 详情 |
Extended Information