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【结 构 式】 
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【分子编号】48074 【品名】N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methyl-2-oxiranecarboxamide 【CA登记号】 |
【 分 子 式 】C12H9F3N2O2 【 分 子 量 】270.2109496 【元素组成】C 53.34% H 3.36% F 21.09% N 10.37% O 11.84% |
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：(IV)Coupling of methacryloyl chloride (I) with substituted aniline (II) in dimethylacetamide yields amide (III), which is then converted into the epoxy derivative (IV) by oxidation with m-chloroperbenzoic acid (mCPBA) and 4-methyl-2,6-di-tert-butylphenol (A) in refluxing 1,1,1-trichloroethane. Condensation of (IV) with thiol (V) by means of NaH in THF provides fluorophenylthio derivative (VI), which is finally oxidized with mCPBA in CH2Cl2 to furnish the desired compound trichloroethane.
| 【1】 Tucker, H. (AstraZeneca plc); Amide derivs.. EP 0100172; JP 1990131462; US 4636505 . |
| 【2】 Crook, J.W.; Tucker, H.; Chesterson, G.J.; Nonsteroidal antiandrogens. Synthesis and structure-activity relationships of 3-substituted derivatives of 2-hydroxypropionanilides. J Med Chem 1988, 31, 5, 954. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 48072 | 2,6-di(tert-butyl)-4-methylphenol | 128-37-0 | C15H24O | 详情 | 详情 |
| (I) | 33553 | 2-methylacryloyl chloride | 920-46-7 | C4H5ClO | 详情 | 详情 |
| (II) | 18743 | 4-amino-2-(trifluoromethyl)benzonitrile；5-Amino-2-cyanobenzotrifluoride | 654-70-6 | C8H5F3N2 | 详情 | 详情 |
| (III) | 48071 | N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methylacrylamide | C12H9F3N2O | 详情 | 详情 | |
| (IV) | 48074 | N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methyl-2-oxiranecarboxamide | C12H9F3N2O2 | 详情 | 详情 | |
| (V) | 22971 | 4-fluorobenzenethiol; 4-fluorophenylhydrosulfide; 4-Fluorothiophenol | 371-42-6 | C6H5FS | 详情 | 详情 |
| (VI) | 48073 | N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfanyl]-2-hydroxy-2-methylpropanamide | C18H14F4N2O2S | 详情 | 详情 |
Extended Information