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【结 构 式】

【分子编号】19195

【品名】3-formylbenzoic acid

【CA登记号】619-21-6

【 分 子 式 】C8H6O3

【 分 子 量 】150.13384

【元素组成】C 64% H 4.03% O 31.97%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(VIII)

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
Extended Information