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【结 构 式】 
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【药物名称】DuP-991 【化学名称】3-(2-Chlorophenyl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-3-buten-2-ol methanesulfonate 【CA登记号】 【 分 子 式 】C19H18ClF2N3O4S 【 分 子 量 】457.88681 |
【开发单位】BTG (Technology Transfer), Bristol-Myers Squibb (Originator) 【药理作用】Antifungal Agents, ANTIINFECTIVE THERAPY |
合成路线1
The intermediate epoxide (IV) was synthesized by two different procedures: 1) The Grignard reagent (II), prepared from 1-bromo-2'-chlorostyrene (I) and Mg, was condensed with 2-chloro-2',4'-difluoroacetophenone (III) to afford epoxide (IV). 2) Alternatively, Wittig reaction of epoxyketone (V) with methylenetriphenylphosphorane provided the target intermediate (IV). The title compound was then obtained by epoxide opening of (IV) with potassium triazole (VI) in DMF at 60 C, and was isolated as the methanesulfonate salt.
| 【1】 Cuomo, J.; Greenberg, R.S.; Olson, R.E. (DuPont Pharmaceuticals Co.); Antifungal carbinols. EP 0251086; JP 1988060975 . |
| 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) | 14366 | 1-(1-bromovinyl)-2-chlorobenzene | C8H6BrCl | 详情 | 详情 | |
| (II) | 14367 | bromo[1-(2-chlorophenyl)vinyl]magnesium | C8H6BrClMg | 详情 | 详情 | |
| (III) | 16321 | 2-Chloro-2',4'-difluoroacetophenone; 2-Chloro-1-(2,4-difluorophenyl)-1-ethanone | 51336-94-8 | C8H5ClF2O | 详情 | 详情 |
| (IV) | 31353 | 2-[1-(2-chlorophenyl)vinyl]-2-(2,4-difluorophenyl)oxirane | C16H11ClF2O | 详情 | 详情 | |
| (V) | 14370 | 1H-1,2,4-triazolium potassium salt | C2H2KN3 | 详情 | 详情 | |
| (VI) | 31354 | (2-chlorophenyl)[2-(2,4-difluorophenyl)-2-oxiranyl]methanone | C15H9ClF2O2 | 详情 | 详情 |