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【结 构 式】 
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【分子编号】28487 【品名】8-(2,4-dichlorophenyl)-2,7-dimethylpyrazolo[1,5-a][1,3,5]triazin-4(3H)-one 【CA登记号】 |
【 分 子 式 】C13H10Cl2N4O 【 分 子 量 】309.15416 【元素组成】C 50.51% H 3.26% Cl 22.94% N 18.12% O 5.18% |
合成路线1
该中间体在本合成路线中的序号：(VI)Claisen condensation of 2,4-dichlorophenylacetonitrile (I) with ethyl acetate using of Na metal gave ketonitrile (II), which was reacted with hydrazine hydrate in the presence of AcOH to afford aminopyrazole (III). Subsequent condensation of (III) with ethyl acetimidate (IV) produced amidine (V). This was cyclized with diethyl carbonate and NaOEt to furnish the pyrazolotriazinone (VI). Chlorination of (VI) using phosphoryl chloride in N,N-dimethylaniline provided chloride (VII), which was finally coupled with 1,3-dimethoxy-2-aminopropane (VIII) to yield the title compound.
| 【1】 Gilligan, P.J.; He, L.; Zaczek, R.; et al.; 4-(1,3-Dimethoxyprop-2-ylamino)-2,7-dimethyl-8-(2,4-dichlorophenyl)pyrazolo[1,5-a]-1,3,5-triazine: A potent, orally bioavailable CRF1 receptor antagonist. J Med Chem 2000, 43, 3, 449. |
| 【2】 Arvanitis, A.G.; Chorvat, R.J. (DuPont Pharmaceuticals Co.); Azolo triazines and pyrimidines. US 6124289; WO 9803510 . |
| 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) | 28484 | 2,4.Dichlorobenzyl cyanide; 2-(2,4-Dichlorophenyl)acetonitrile | 6306-60-1 | C8H5Cl2N | 详情 | 详情 |
| (II) | 28485 | 2-(2,4-dichlorophenyl)-3-oxobutanenitrile | C10H7Cl2NO | 详情 | 详情 | |
| (III) | 27688 | 4-(2,4-dichlorophenyl)-3-methyl-1H-pyrazol-5-amine | C10H9Cl2N3 | 详情 | 详情 | |
| (IV) | 12831 | ethyl ethanimidoate | 1000-84-6 | C4H9NO | 详情 | 详情 |
| (V) | 28486 | N-[4-(2,4-dichlorophenyl)-3-methyl-1H-pyrazol-5-yl]ethanimidamide | C12H12Cl2N4 | 详情 | 详情 | |
| (VI) | 28487 | 8-(2,4-dichlorophenyl)-2,7-dimethylpyrazolo[1,5-a][1,3,5]triazin-4(3H)-one | C13H10Cl2N4O | 详情 | 详情 | |
| (VII) | 28488 | 4-chloro-8-(2,4-dichlorophenyl)-2,7-dimethylpyrazolo[1,5-a][1,3,5]triazine | C13H9Cl3N4 | 详情 | 详情 | |
| (VIII) | 23336 | 1,3-dimethoxy-2-propanamine | C5H13NO2 | 详情 | 详情 |