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【结 构 式】 
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【药物名称】ILX-295501, LY-295501 【化学名称】1-(3,4-Dichlorophenyl)-3-(2,3-dihydrobenzofuran-5-ylsulfonyl)urea 【CA登记号】150869-74-2 【 分 子 式 】C15H12Cl2N2O4S 【 分 子 量 】387.24389 |
【开发单位】Lilly (Originator), Ilex Oncology (Codevelopment) 【药理作用】Lung Cancer Therapy, Melanoma Therapy, Non-Small Cell Lung Cancer Therapy, Oncolytic Drugs, Ovarian Cancer Therapy, Renal Cancer Therapy, Sulfonylureas |
合成路线1
Electrophilic sulfonation of 2,3-dihydrobenzofuran (I) using sulfur trioxide-dimethylformamide complex produced sulfonic acid (II), which was subsequently converted into the sulfonyl chloride (III) by chlorination with SOCl2. Reaction of sulfonyl chloride (III) with a solution of ammonia in cold dichloroethane gave rise to the sulfonamide (IV). This was subsequently condensed with 3,4-dichlophenyl isocyanate (V) to furnish the target sulfonyl urea
| 【1】 Tao, E.V.-P.; Miller, W.D. (Eli Lilly and Company); Synthesis of bicyclic aromatic sulfonic acids, sulfonyl chlorides and sulfonamides. EP 0583960 . |
| 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) | 14499 | 2,3-Dihydrobenzofuran; 2,3-dihydro-1-benzofuran | 496-16-2 | C8H8O | 详情 | 详情 |
| (II) | 59847 | 2,3-dihydro-1-benzofuran-5-sulfonic acid | C8H8O4S | 详情 | 详情 | |
| (III) | 59848 | 2,3-dihydro-1-benzofuran-5-sulfonyl chloride | C8H7ClO3S | 详情 | 详情 | |
| (IV) | 59849 | 2,3-dihydro-1-benzofuran-5-sulfonamide | C8H9NO3S | 详情 | 详情 | |
| (V) | 34282 | 1,2-dichloro-4-isocyanatobenzene; 3,4-dichlorophenyl isocyanate | 102-36-3 | C7H3Cl2NO | 详情 | 详情 |