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【结 构 式】 
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【分子编号】48187 【品名】3-[[(3,4-dimethyl-5-isoxazolyl)(methoxymethyl)amino]sulfonyl]-2-thiophenecarboxylic acid 【CA登记号】 |
【 分 子 式 】C12H14N2O6S2 【 分 子 量 】346.38504 【元素组成】C 41.61% H 4.07% N 8.09% O 27.71% S 18.51% |
合成路线1
该中间体在本合成路线中的序号：(V)Coupling between 2-(methoxycarbonyl)-3-thiophenesulfonyl chloride (I) and 5-amino-3,4-dimethylisoxazole (II) afforded the corresponding sulfonamide (III). The sulfonamide NH group of (III) was then protected by reaction with bromomethyl methyl ether to produce the methoxymethyl derivative (IV). Basic hydrolysis of the methyl ester function of (IV), followed by treatment of the resultant carboxylic acid (V) with oxalyl chloride, furnished the acid chloride (VI). This was then coupled with 2'-amino-3',5'-dimethylacetophenone (VII) to yield amide (VIII). The methoxymethyl protecting group of (VIII) was finally removed by acidic treatment to provide the title compound.
| 【1】 Blok, N.; Holland, G.W.; Wu, C. (Texas Biotechnology Corp.); Sulfonamides and derivs. thereof that modulate the activity of endothelin. WO 0149685 . |
| 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) | 17836 | Methyl 3-(chlorosulfonyl)-2-thiophenecarboxylate; Methyl-3-chlorosulfonylthiophene-2-carboxylate | C6H5ClO4S2 | 详情 | 详情 | |
| (II) | 26891 | 3,4-dimethyl-5-isoxazolamine | 19947-75-2 | C5H8N2O | 详情 | 详情 |
| (III) | 48185 | methyl 3-[[(3,4-dimethyl-5-isoxazolyl)amino]sulfonyl]-2-thiophenecarboxylate | C11H12N2O5S2 | 详情 | 详情 | |
| (IV) | 48186 | methyl 3-[[(3,4-dimethyl-5-isoxazolyl)(methoxymethyl)amino]sulfonyl]-2-thiophenecarboxylate | C13H16N2O6S2 | 详情 | 详情 | |
| (V) | 48187 | 3-[[(3,4-dimethyl-5-isoxazolyl)(methoxymethyl)amino]sulfonyl]-2-thiophenecarboxylic acid | C12H14N2O6S2 | 详情 | 详情 | |
| (VI) | 48188 | 3-[[(3,4-dimethyl-5-isoxazolyl)(methoxymethyl)amino]sulfonyl]-2-thiophenecarbonyl chloride | C12H13ClN2O5S2 | 详情 | 详情 | |
| (VII) | 47990 | 1-(2-amino-3,5-dimethylphenyl)-1-ethanone | C10H13NO | 详情 | 详情 | |
| (VIII) | 48189 | N-(2-acetyl-4,6-dimethylphenyl)-3-[[(3,4-dimethyl-5-isoxazolyl)(methoxymethyl)amino]sulfonyl]-2-thiophenecarboxamide | C22H25N3O6S2 | 详情 | 详情 |