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【结 构 式】 
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【分子编号】19196 【品名】N-(4-[2-[6,7-dimethoxy-3,4-dihydro-2(1H)-isoquinolinyl]ethyl]phenyl)-3-formylbenzamide 【CA登记号】 |
【 分 子 式 】C27H28N2O4 【 分 子 量 】444.5304 【元素组成】C 72.95% H 6.35% N 6.3% O 14.4% |
合成路线1
该中间体在本合成路线中的序号：(IX)Condensation of 1,4-diacetyl-2,5-piperazinedione (I) with the equimolecular amount of benzaldehyde in the presence of triethylamine affords the benzylidene compound (II), which is N-methylated on treatment with iodomethane and sodium hydride to give III. Alkylation of the tetrahydroisoquinoline (V) with 4-(2-bromoethyl)nitrobenzene (IV) provides the tertiary amine (VI). The nitro group of (VI) is reduced by treatment with iron powder and concentrated HCl in refluxing MeOH to give aniline VII, which is condensed with 3-formylbenzoic acid (VIII) in the presence of 2-chloro-1-methylpyridinium iodide to afford the corresponding amide (IX). Finally, condensation between the previously obtained piperazinedione (III) and aldehyde (IX) in the presence of Cs2CO3 leads to the title compound.
| 【1】 Ashworth, P.A.; Hunjan, S.; Pretswell, I.A.; Ryder, H.; Brocchini, S.J. (Xenova Group plc); Piperazine-2,5-dione derivs. as modulators of multidrug resistance. EP 0799210; GB 2311780; JP 1998511385; US 5935955; WO 9620180 . |
| 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) | 19188 | 1,4-diacetyl-2,5-piperazinedione;N,N'-DIACETYLGLYCINE ANHYDRIDE;1,4-DIACETYL-PIPERAZINE-2,5-DIONE;1,4-DIACETYLTETRAHYDRO-2,5-PYRAZINEDIONE;1,4-DIACETYL-2,5-DIKETOPIPERAZINE;1,4-DIACETYL-2,5-DIOXOPIPERAZINE | 3027-05-2 | C8H10N2O4 | 详情 | 详情 |
| (II) | 19189 | 1-acetyl-3-[(Z)-benzylidene]-2,5-piperazinedione | C13H12N2O3 | 详情 | 详情 | |
| (III) | 19190 | 1-acetyl-4-methyl-3-[(Z)-benzylidene]-2,5-piperazinedione | C14H14N2O3 | 详情 | 详情 | |
| (IV) | 19191 | 1-(2-bromoethyl)-4-nitrobenzene | 5339-26-4 | C8H8BrNO2 | 详情 | 详情 |
| (V) | 19192 | 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride | 2328-12-3 | C11H16ClNO2 | 详情 | 详情 |
| (VI) | 19193 | 6,7-dimethoxy-2-(4-nitrophenethyl)-1,2,3,4-tetrahydroisoquinoline; 6-methoxy-2-(4-nitrophenethyl)-1,2,3,4-tetrahydro-7-isoquinolinyl methyl ether | C19H22N2O4 | 详情 | 详情 | |
| (VII) | 19194 | 4-[2-[6,7-dimethoxy-3,4-dihydro-2(1H)-isoquinolinyl]ethyl]aniline; 4-[2-[6,7-dimethoxy-3,4-dihydro-2(1H)-isoquinolinyl]ethyl]phenylamine | C19H24N2O2 | 详情 | 详情 | |
| (VIII) | 19195 | 3-formylbenzoic acid | 619-21-6 | C8H6O3 | 详情 | 详情 |
| (IX) | 19196 | N-(4-[2-[6,7-dimethoxy-3,4-dihydro-2(1H)-isoquinolinyl]ethyl]phenyl)-3-formylbenzamide | C27H28N2O4 | 详情 | 详情 |