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【结 构 式】

【分子编号】21463

【品名】2-cyano-N-(2,5-dibromophenyl)acetamide

【CA登记号】

【 分 子 式 】C9H6Br2N2O

【 分 子 量 】317.96752

【元素组成】C 34% H 1.9% Br 50.26% N 8.81% O 5.03%

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:(VI)

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
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