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【结 构 式】 
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【分子编号】34492 【品名】phenyl 3-(5-chloro-3-thienyl)-4-oxo-2,4-dihydroindeno[1,2-c]pyrazol-5-ylcarbamate 【CA登记号】 |
【 分 子 式 】C21H12ClN3O3S 【 分 子 量 】421.8634 【元素组成】C 59.79% H 2.87% Cl 8.4% N 9.96% O 11.38% S 7.6% |
合成路线1
该中间体在本合成路线中的序号：(VIII)Dimethyl 3-nitrophthalate (I) was hydrogenated in the presence of Pd/C to give aminophthalate (II), which was acylated with Ac2O in pyridine, yielding acetamidophthalate (III). Condensation of phthalate ester (III) with 4-acetyl-2-chlorothiophene (IV) using NaH in DMF produced triketone (V). After acid hydrolysis of the amide function of (V), the resulting aminoindenetrione (VI) was cyclized with hydrazine hydrate to generate the indenopyrazolone system (VII). Condensation of (VII) with phenyl chloroformate afforded the phenyl carbamate (VIII). This was finally treated with concentrated ammonia to furnish the target urea derivative.
| 【1】 Yue, E.W.; Carini, D.J.; Nugiel, D.A.; Dimeo, S.V. (DuPont Pharmaceuticals Co.); 5-Aminoindeno(1,2-c)pyrazol-4-ones as anti-cancer and anti-proliferative agents. WO 9954308 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 13580 | 1-[(Chlorocarbonyl)oxy]benzene; phenyl chloroformate | 1885-14-9 | C7H5ClO2 | 详情 | 详情 | |
| (I) | 34481 | dimethyl 3-nitrophthalate | 13365-26-9 | C10H9NO6 | 详情 | 详情 |
| (II) | 34482 | dimethyl 3-aminophthalate | C10H11NO4 | 详情 | 详情 | |
| (III) | 34483 | dimethyl 3-(acetamido)phthalate | C12H13NO5 | 详情 | 详情 | |
| (IV) | 34488 | 1-(5-chloro-3-thienyl)-1-ethanone | C6H5ClOS | 详情 | 详情 | |
| (V) | 34489 | N-[2-[(5-chloro-3-thienyl)carbonyl]-1,3-dioxo-2,3-dihydro-1H-inden-4-yl]acetamide | C16H10ClNO4S | 详情 | 详情 | |
| (VI) | 34490 | 4-amino-2-[(5-chloro-3-thienyl)carbonyl]-1H-indene-1,3(2H)-dione | C14H8ClNO3S | 详情 | 详情 | |
| (VII) | 34491 | 5-amino-3-(5-chloro-3-thienyl)indeno[1,2-c]pyrazol-4(2H)-one | C14H8ClN3OS | 详情 | 详情 | |
| (VIII) | 34492 | phenyl 3-(5-chloro-3-thienyl)-4-oxo-2,4-dihydroindeno[1,2-c]pyrazol-5-ylcarbamate | C21H12ClN3O3S | 详情 | 详情 |