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【结 构 式】 
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【药物名称】NGB-2904 【化学名称】N-[4-[4-(2,3-Dichlorophenyl)piperazin-1-yl]butyl]fluorene-2-carboxamide 【CA登记号】189061-11-8 (monoHCl) 【 分 子 式 】C28H29Cl2N3O 【 分 子 量 】494.46883 |
【开发单位】Neurogen (Originator) 【药理作用】Antipsychotic Drugs, Pharmacological Tools, PSYCHOPHARMACOLOGIC DRUGS, Dopamine D3 Antagonists |
合成路线1
Dichlorophenylpiperazine (III) was prepared from aniline (I) by dehydrative cyclization with diethanolamine (II) in the presence of P2O5 and Et3N-HCl at 200 C. Alkylation of piperazine (III) with N-(4-bromobutyl) phthalimide (IV) gave (V), and subsequent hydrazinolysis of the phthalimide provided the (4-aminobutyl)piperazine (VI). Finally, condensation of (VI) with fluorene-2-carboxylic acid (VII) yielded the target amide.
| 【1】 Yuan, J.; Chen, X.; Brodbeck, R.; Primus, R.; Braun, J.; Wasley, W.F.; Thurkauf, A.; NGB 2904 and NGB 2849: Two highly selective dopamine D3 receptor antagonists. Bioorg Med Chem Lett 1998, 8, 19, 2715. |
| 【2】 Yuan, J.; Chen, X. (Neurogen Corp.); Novel N-aminoalkylfluorenecarboxamides; a new class of dopamine receptor subtype specific ligands. EP 0873329; JP 1998511114; US 5659033; WO 9710229 . |
| 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) | 28562 | 2,3-dichlorophenylamine | 608-27-5 | C6H5Cl2N | 详情 | 详情 |
| (II) | 24273 | 2-[(2-hydroxyethyl)amino]-1-ethanol | 111-42-2 | C4H11NO2 | 详情 | 详情 |
| (III) | 13943 | 1-(2,3-Dichlorophenyl)piperazine | 41202-77-1 | C10H12Cl2N2 | 详情 | 详情 |
| (IV) | 17163 | N-(4-Bromobutyl)phthalimide; 2-(4-Bromobutyl)-1H-isoindole-1,3(2H)-dione | 5394-18-3 | C12H12BrNO2 | 详情 | 详情 |
| (V) | 28563 | 2-[4-[4-(2,3-dichlorophenyl)-1-piperazinyl]butyl]-1H-isoindole-1,3(2H)-dione | C22H23Cl2N3O2 | 详情 | 详情 | |
| (VI) | 28564 | 4-[4-(2,3-dichlorophenyl)-1-piperazinyl]butylamine | C14H21Cl2N3 | 详情 | 详情 | |
| (VII) | 28566 | 9H-fluorene-2-carboxylic acid | C14H10O2 | 详情 | 详情 |
Extended Information