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【结 构 式】 
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【分子编号】68645 【品名】N-(6-chloro-5-methylpyridin-2-yl)pivalamide 【CA登记号】 |
【 分 子 式 】C11H15ClN2O 【 分 子 量 】226.70568 【元素组成】C 58.28% H 6.67% Cl 15.64% N 12.36% O 7.06% |
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：(XXI)The intermediate 6-amino-2-chloro-3-methylpyridine (XIII) is prepared by protection of 2-amino-5-methylpyridine (XVIII) with pivaloyl chloride in the presence of Et3N in CH2Cl2 to give the N-pyridyl pivalamide (XIX), which is converted to the corresponding N-oxide (XX) by treatment with H2O2 in AcOH at 80 °C. Rearrangement of the N-oxide (XX) by means of POCl3 and Et3N in refluxing CH2Cl2 leads to the chloropyridine (XXI), which is finally hydrolyzed with aqueous HCl at 80 °C .
| 【1】 Hadida Rua, S., Hamilton, M., Miller, M., Grootenhuis, P.D.J., Bear, B., McCarthy, J., Zhou, J. (Vertex Pharmaceuticals, Inc.). Heterocyclic modulators of ATP-binding cassette transporters. EP 1945632, EP 2395002, EP 2404919, JP 2009514962, US 2008113985, US 7741321, US 7973038, US 2011172229, US 2011312958, US 2012232059, WO 2007056341. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XIII) | 68639 | 6-amino-2-chloro-3-methylpyridine;2-Amino-6-chloro-5-methylpyridine;6-chloro-5-methyl-2-Pyridinamine | 442129-37-5 | C6H7ClN2 | 详情 | 详情 |
| (XVIII) | 12752 | 5-Methyl-2-pyridinylamine; 2-Amino-5-methylpyridine; 5-Methyl-2-pyridinamine; 6-Amino-beta-picoline; 6-Amino-3-picoline | 1603-41-4 | C6H8N2 | 详情 | 详情 |
| (XIX) | 68643 | N-(5-methylpyridin-2-yl)pivalamide | C11H16N2O | 详情 | 详情 | |
| (XX) | 68644 | 5-methyl-2-pivalamidopyridine 1-oxide | C11H16N2O2 | 详情 | 详情 | |
| (XXI) | 68645 | N-(6-chloro-5-methylpyridin-2-yl)pivalamide | C11H15ClN2O | 详情 | 详情 |
Extended Information