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【结 构 式】 
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【分子编号】21460 【品名】N-(2,5-dibromophenyl)-5-methyl-4-isoxazolecarboxamide 【CA登记号】 |
【 分 子 式 】C11H8Br2N2O2 【 分 子 量 】360.0048 【元素组成】C 36.7% H 2.24% Br 44.39% N 7.78% O 8.89% |
合成路线1
该中间体在本合成路线中的序号：(III)Title compound has been prepared by two synthetic ways: 1) Condensation of the acetoacetanilide (I) with triethyl orthoformate in the presence of Ac2O provided the ethoxymethylene compound (II), which was reacted with hydroxylamine in methanol-water to afford isoxazole (III). Ring opening of the heterocycle with NaOH then gave the target cyanoacetanilide. 2) In a different procedure, cyanoacetic acid (V) was coupled with 2,5-dibromoaniline (IV) in the presence of diisopropyl carbodiimide (DIC) to form cyanoacetanilide (VI), which was acylated using acetyl chloride and NaH to afford the hydroxyethylidene derivative.
| 【1】 Ghosh, S.; Zheng, Y.; Jun, X.; Narla, R.K.; Mahajan, S.; Navara, C.; Mao, C.; Sudbeck, E.A.; Uckun, F.M.; alpha-Cyano-beta-hydroxy-beta-methyl-N-[4-(trifluoromethoxy)phenyl]propenamide: An inhibitor of the epidermal growth factor receptor tyrosine kinase with potent cytotoxic activity. Clin Cancer Res 1998, 4, 11, 2657. |
| 【2】 Ertel, H.; Wolf, E.; Heubach, G. (Aventis SA); Cyano acetic acid anilide derivs., process for their manufacture and compsns. containing these cpds.. DE 2524929; US 4061767 . |
| 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) | 21458 | N-(2,5-dibromophenyl)-3-oxobutanamide | C10H9Br2NO2 | 详情 | 详情 | |
| (II) | 21459 | (E)-2-acetyl-N-(2,5-dibromophenyl)-3-ethoxy-2-propenamide | C13H13Br2NO3 | 详情 | 详情 | |
| (III) | 21460 | N-(2,5-dibromophenyl)-5-methyl-4-isoxazolecarboxamide | C11H8Br2N2O2 | 详情 | 详情 | |
| (IV) | 21461 | 2,5-dibromoaniline; 2,5-dibromophenylamine | 3638-73-1 | C6H5Br2N | 详情 | 详情 |
| (V) | 12591 | Cyanoacetic Acid; 2-Cyanoacetic acid | 372-09-8 | C3H3NO2 | 详情 | 详情 |
| (VI) | 21463 | 2-cyano-N-(2,5-dibromophenyl)acetamide | C9H6Br2N2O | 详情 | 详情 |