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【结 构 式】 
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【药物名称】DO-897, BP-4.897, BP-897 【化学名称】N-[4-[4-(2-Methoxyphenyl)-1-piperazinyl]butyl]naphthalene-2-carboxamide 【CA登记号】192384-87-5 【 分 子 式 】C26H31N3O2 【 分 子 量 】417.55587 |
【开发单位】Bioprojet (Originator), INSERM (Originator) 【药理作用】Treatment of Cocaine Dependency, TREATMENT OF POISONING, DRUG ABUSE & DEPENDENCY, Treatment of Substance Dependency, Dopamine D3 Agonists |
合成路线1
N-(2-Methoxyphenyl)piperazine (I) was alkylated with 4-bromobutyronitrile (II) to provide the 3-cyanopropylpiperazine (III). Subsequent reduction of the cyano group of (III) using LiAlH4 produced the primary amine (IV). The title amide was then obtained by condensation of (IV) with 2-naphthoic acid (V) after activation as the corresponding acid chloride with (COCl)2 or as the mixed anhydride with isobutyl chloroformate.
| 【1】 Mann, A.; Sokoloff, P.; Schwartz, J.-C.; Wermuth, C.-G.; Garrido, F.; Lecomte, J.-M. (INSERM (Institut National de la Sante et de la Recherche Medicale); Societe Civile Bioprojet); 2-Naphthamide derivs. and their therapeutic applications. EP 0779284; FR 2742149; US 5872119; US 5985895 . |
| 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) | 11882 | 1-(2-Methoxyphenyl)piperazine; Methyl 2-piperazinophenyl ether; 1-(2-Methoxyphenyl)-piperazine | 35386-24-4 | C11H16N2O | 详情 | 详情 |
| (II) | 34789 | 4-bromobutanenitrile | 5332-06-9 | C4H6BrN | 详情 | 详情 |
| (III) | 34790 | 4-[4-(2-methoxyphenyl)-1-piperazinyl]butanenitrile | C15H21N3O | 详情 | 详情 | |
| (IV) | 34791 | 4-[4-(2-methoxyphenyl)-1-piperazinyl]butylamine; 4-[4-(2-methoxyphenyl)-1-piperazinyl]-1-butanamine | C15H25N3O | 详情 | 详情 | |
| (V) | 34792 | 2-naphthoic acid | 93-09-4 | C11H8O2 | 详情 | 详情 |