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【结 构 式】 
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【分子编号】47948 【品名】methyl 2-bromo-2-(3,4-dichlorophenyl)acetate 【CA登记号】 |
【 分 子 式 】C9H7BrCl2O2 【 分 子 量 】297.96278 【元素组成】C 36.28% H 2.37% Br 26.82% Cl 23.8% O 10.74% |
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：(VI)Reaction of 2-chloropyrazine (I) with 3,4-dichlorophenylmagnesium bromide (II) in the presence of [1,2-bis(diphenylphosphino)ethane]nickel(II) chloride produced the 2-arylpyrazine (III), which was reduced to the corresponding piperazine (IV) by means of DIBAL in THF. In a different procedure, bromination of methyl 3,4-dichlorophenylacetate (V) using N-bromosuccinimide, followed by reaction of the resulting bromo ester (VI) with ethylenediamine (VII) afforded the piperazinone (VIII), which was further reduced to (IV) by using LiAlH4 in Et2O.
| 【1】 Anthes, J.C.; McPhail, A.T.; Blythin, D.J.; Shue, H.-J.; Chen, X.; Piwinski, J.J.; shih, N.-Y.; Discovery of Sch 62373 and analogs, of novel series of 2-phenylpiperazines exhibiting potent dual NK1/NK2 antagonist activity. 221st ACS Natl Meet (April 1 2001, San Diego) 2001, Abst MEDI 244. |
| 【2】 Shue, H.-J.; Shih, N.-Y.; Blythin, D.J.; Chen, X.; Tom, W.C.; Piwinski, J.J.; McCormick, K.D. (Schering Corp.); Piperazino derivs. as neurokinin antagonists. EP 0823906; US 5719156; WO 9634864 . |
| 【3】 Piwinski, J.J.; McCormick, K.D.; Shue, H.-J.; Chen, X.; Shih, N.-Y.; Blythin, D.J. (Schering Corp.); Piperazino derivs. as neurokinin antagonists. EP 0850236; JP 2000344766; US 5795894; US 5892039; WO 9708166 . |
| 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) | 24075 | 2-chloropyrazine | 14508-49-7 | C4H3ClN2 | 详情 | 详情 |
| (II) | 10069 | Bromo(3,4-dichlorophenyl)magnesium | 79175-35-2 | C6H3BrCl2Mg | 详情 | 详情 |
| (III) | 47945 | 2-(3,4-dichlorophenyl)pyrazine | C10H6Cl2N2 | 详情 | 详情 | |
| (IV) | 47946 | 2-(3,4-dichlorophenyl)piperazine | C10H12Cl2N2 | 详情 | 详情 | |
| (V) | 47947 | methyl 2-(3,4-dichlorophenyl)acetate | C9H8Cl2O2 | 详情 | 详情 | |
| (VI) | 47948 | methyl 2-bromo-2-(3,4-dichlorophenyl)acetate | C9H7BrCl2O2 | 详情 | 详情 | |
| (VII) | 14754 | ethylenediamine;1,2-Diaminoethane;ethane-1,2-diamine；1,2-Ethanediamine | 107-15-3 | C2H8N2 | 详情 | 详情 |
| (VIII) | 47949 | 3-(3,4-dichlorophenyl)-2-piperazinone | C10H10Cl2N2O | 详情 | 详情 |
Extended Information