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【结 构 式】 
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【药物名称】TBC-10894, IPI-894 【化学名称】N-(4-Bromo-3-methylisoxazol-5-yl)-5-(4-methylphenyl)thiophene-2-sulfonamide 【CA登记号】 【 分 子 式 】C15H13BrN2O3S2 【 分 子 量 】413.31446 |
【开发单位】Encysive Pharmaceuticals (Originator) 【药理作用】Pharmacological Tools, Endothelin ETB Receptor Antagonists |
合成路线1
Suzuki coupling of 4-tolylboronic acid (I) with 2-bromothiophene (II) under palladium catalysis provided tolylthiophene (III). Subsequent chlorosulfonation of (III) with chlorosulfonic acid in the presence of PCl5 and POCl3 afforded sulfonyl chloride (IV), which was finally condensed with the aminoisoxazole (V) using NaH in THF to furnish the target sulfonamide.
| 【1】 Chan, M.F.; Kois, A.; Verner, E.J.; Raju, B.G.; Castillo, R.S.; Wu, C.; Okun, I.; Stavros, F.D.; Balaji, V.N.; The discovery and structure-activity relationships of nonpeptide, low molecular weight antagonists selective for the endothelin ETB receptor. Bioorg Med Chem 1998, 6, 12, 2301. |
| 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) | 15540 | 4-methylphenylboronic acid; p-Tolylboronic acid | 5720-05-8 | C7H9BO2 | 详情 | 详情 |
| (II) | 13681 | 2-Bromothiophene | 1003-09-4 | C4H3BrS | 详情 | 详情 |
| (III) | 22380 | 2-(4-methylphenyl)thiophene | C11H10S | 详情 | 详情 | |
| (IV) | 22381 | 5-(4-methylphenyl)-2-thiophenesulfonyl chloride | C11H9ClO2S2 | 详情 | 详情 | |
| (V) | 22382 | 4-bromo-3-methyl-5-isoxazolamine; 4-bromo-3-methyl-5-isoxazolylamine | C4H5BrN2O | 详情 | 详情 |
Extended Information