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【结 构 式】 
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【分子编号】21253 【品名】N-(tert-butyl)-4-[1-hydroxy-4-[1-(trimethylsilyl)-1H-imidazol-4-yl]butyl]benzamide 【CA登记号】 |
【 分 子 式 】C21H33N3O2Si 【 分 子 量 】387.59754 【元素组成】C 65.08% H 8.58% N 10.84% O 8.26% Si 7.25% |
合成路线1
该中间体在本合成路线中的序号：(IX)2) The protection of 4-[3-(ethoxycarbonyl)propyl-1H-imidazole (VI) with trimethylsilyl chloride followed by reduction with diisobutylaluminum hydride (DBAH) in dichloromethane gives 4-(3-formylpropyl)-1-(trimethylsilyl)imidazole (VII), which is condensed with 4-(tert-butylcarbamoyl)bromobenzene (VIII) by means of butyllithium in THF yielding 4-[4-[4-(tert-butylcarbamoyl)phenyl]-4-hydroxybutyl]-1-(trimethylsilyl) imidazole (IX). The reaction of (IX) with refluxing SOCl2 affords 4-[4-chloro-4-(4-cyanophenyl)butyl]-1H-imidazole (X), which is finally cyclized in refluxing CHCl3.
| 【1】 Browne, L.J. (Ciba Geigy Corp.); Substituted imidazo[1,5-A]pyridine derivatives as aromatase inhibitors.. ES 8801262; JP 61012688; US 4617307 . |
| 【2】 Pento, J.T.; Prous, J.; Castaner, J.; CGS-16949A. Drugs Fut 1989, 14, 9, 843. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VI) | 21250 | ethyl 4-(1H-imidazol-4-yl)butanoate | C9H14N2O2 | 详情 | 详情 | |
| (VII) | 21251 | 4-[1-(trimethylsilyl)-1H-imidazol-4-yl]butanal | C10H18N2OSi | 详情 | 详情 | |
| (VIII) | 21252 | 4-bromo-N-(tert-butyl)benzamide | C11H14BrNO | 详情 | 详情 | |
| (IX) | 21253 | N-(tert-butyl)-4-[1-hydroxy-4-[1-(trimethylsilyl)-1H-imidazol-4-yl]butyl]benzamide | C21H33N3O2Si | 详情 | 详情 | |
| (X) | 21254 | 4-[1-chloro-4-(1H-imidazol-4-yl)butyl]benzonitrile | C14H14ClN3 | 详情 | 详情 |