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【结 构 式】 
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【分子编号】47294 【品名】4-[[5-(hydroxymethyl)-2-sulfanyl-1H-imidazol-1-yl]methyl]benzonitrile 【CA登记号】 |
【 分 子 式 】C12H11N3OS 【 分 子 量 】245.30496 【元素组成】C 58.76% H 4.52% N 17.13% O 6.52% S 13.07% |
合成路线1
该中间体在本合成路线中的序号：(XXII)In a further procedure, bromide (XV) was reacted with hexamethylenetetramine in refluxing EtOH followed by acid hydrolysis to produce the benzyl amine (XX). Mercapto imidazole (XXII) was then obtained by condensation of amine (XX) with dihydroxyacetone (XXI) and KSCN. Subsequent oxidative desulfuration gave the hydroxymethyl imidazole (XVIII). This was converted to the corresponding chloride (XXIII) by treatment with either SOCl2 in DMF or the Vilsmeier reagent. Finally, chloride (XXIII) was condensed with piperazinone (VIII) in the presence of diisopropylethylamine.
| 【1】 Cowen, J.A.; Askin, D.; McWilliams, J.C.; Maligres, P.E.; McCauley, J.A. (Merck & Co., Inc.); Process for making farnesyl-protein transferase inhibitors. WO 0001691 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VIII) | 47289 | 1-(3-chlorophenyl)-2-piperazinone | C10H11ClN2O | 详情 | 详情 | |
| (XV) | 14200 | 4-(Bromomethyl)benzonitrile; alpha-Bromo-p-tolunitrile | 17201-43-3 | C8H6BrN | 详情 | 详情 |
| (XVIII) | 38389 | 4-[[5-(hydroxymethyl)-1H-imidazol-1-yl]methyl]benzonitrile | C12H11N3O | 详情 | 详情 | |
| (XX) | 47293 | 4-(aminomethyl)benzonitrile | C8H8N2 | 详情 | 详情 | |
| (XXI) | 14575 | Dihydroxyacetone; 1,3-dihydroxyacetone | 96-26-4 | C3H6O3 | 详情 | 详情 |
| (XXII) | 47294 | 4-[[5-(hydroxymethyl)-2-sulfanyl-1H-imidazol-1-yl]methyl]benzonitrile | C12H11N3OS | 详情 | 详情 | |
| (XXIII) | 47295 | 4-[[5-(chloromethyl)-1H-imidazol-1-yl]methyl]benzonitrile | C12H10ClN3 | 详情 | 详情 |