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【结 构 式】 
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【分子编号】49762 【品名】N-[3-(4-methoxyphenyl)-4-oxo-2,4-dihydroindeno[1,2-c]pyrazol-5-yl]acetamide 【CA登记号】 |
【 分 子 式 】C19H15N3O3 【 分 子 量 】333.34652 【元素组成】C 68.46% H 4.54% N 12.61% O 14.4% |
合成路线1
该中间体在本合成路线中的序号：(VI)Catalytic hydrogenation of dimethyl 3-nitrophthalate (I) in the presence of Pd/C afforded the corresponding amino derivative (II), which was subsequently acetylated with Ac2O in pyridine yielding amide (III). Claisen condensation of diester (III) with 4'-methoxyacetophenone (IV) using NaH in hot DMF furnished the indandione (V). The tricarbonyl intermediate (V) was then treated with hydrazine to give the indenopyrazole (VI) as a single regioisomer. Acidic hydrolysis of the acetamide function of (VI) provided amine (VII). This was finally converted to the target formamide derivative upon heating with neat formic acid.
| 【1】 Nugiel, D.A.; et al.; Indenopyrazoles as novel cyclin dependen kinase (CDK) inhibitors. J Med Chem 2001, 44, 9, 1334. |
| 【2】 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 |
|---|---|---|---|---|---|---|
| (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) | 11041 | 4-Methoxyacetophenone; 1-(4-Methoxyphenyl)-1-ethanone | 100-06-1 | C9H10O2 | 详情 | 详情 |
| (V) | 34484 | N-[2-(4-methoxybenzoyl)-1,3-dioxo-2,3-dihydro-1H-inden-4-yl]acetamide | C19H15NO5 | 详情 | 详情 | |
| (VI) | 49762 | N-[3-(4-methoxyphenyl)-4-oxo-2,4-dihydroindeno[1,2-c]pyrazol-5-yl]acetamide | C19H15N3O3 | 详情 | 详情 | |
| (VII) | 34486 | 5-amino-3-(4-methoxyphenyl)indeno[1,2-c]pyrazol-4(2H)-one | C17H13N3O2 | 详情 | 详情 |