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【结 构 式】 
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【分子编号】43374 【品名】4-chloro-8-(2,4-dimethoxy-6-methylphenyl)-2,7-dimethylpyrazolo[1,5-a][1,3,5]triazine; 2-(4-chloro-2,7-dimethylpyrazolo[1,5-a][1,3,5]triazin-8-yl)-5-methoxy-3-methylphenyl methyl ether 【CA登记号】 |
【 分 子 式 】C16H17ClN4O2 【 分 子 量 】332.78944 【元素组成】C 57.75% H 5.15% Cl 10.65% N 16.84% O 9.62% |
合成路线1
该中间体在本合成路线中的序号：(VIII)The condensation of 2,4-dimethoxy-6-methylphenylacetonitrile (I) with ethyl acetate in the presence of Na metal produced keto nitrile (II). This was cyclized to the amino pyrazole (III) upon treatment with hydrazine and HOAc in refluxing toluene. Subsequent condensation of amino pyrazole (III) with ethyl acetimidate (IV) gave amidine (V), which was converted to the required pyrazolo triazinone (VI) by reaction with diethyl carbonate and NaOEt. Chlorination of (VI) with POCl3 in the presence of N,N-dimethylaniline produced the chloro derivative (VII). This was finally condensed with amine (VIII) to furnish the title compound.
| 【1】 He, L.; Arvanitis, A.G.; Chorvat, R.; Gilligan, P. (DuPont Pharmaceuticals Co.); Azolo triazines and pyrimidines. EP 1049699; WO 9938868 . |
| 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) | 43369 | 2-(2,4-dimethoxy-6-methylphenyl)acetonitrile | C11H13NO2 | 详情 | 详情 | |
| (II) | 43370 | 2-(2,4-dimethoxy-6-methylphenyl)-3-oxobutanenitrile | C13H15NO3 | 详情 | 详情 | |
| (III) | 43371 | 4-(2,4-dimethoxy-6-methylphenyl)-3-methyl-1H-pyrazol-5-ylamine; 4-(2,4-dimethoxy-6-methylphenyl)-3-methyl-1H-pyrazol-5-amine | C13H17N3O2 | 详情 | 详情 | |
| (IV) | 43372 | N-[4-(2,4-dimethoxy-6-methylphenyl)-3-methyl-1H-pyrazol-5-yl]ethanimidamide | C15H20N4O2 | 详情 | 详情 | |
| (V) | 12831 | ethyl ethanimidoate | 1000-84-6 | C4H9NO | 详情 | 详情 |
| (VI) | 43372 | N-[4-(2,4-dimethoxy-6-methylphenyl)-3-methyl-1H-pyrazol-5-yl]ethanimidamide | C15H20N4O2 | 详情 | 详情 | |
| (VII) | 43373 | 8-(2,4-dimethoxy-6-methylphenyl)-2,7-dimethylpyrazolo[1,5-a][1,3,5]triazin-4(3H)-one | C16H18N4O3 | 详情 | 详情 | |
| (VIII) | 43374 | 4-chloro-8-(2,4-dimethoxy-6-methylphenyl)-2,7-dimethylpyrazolo[1,5-a][1,3,5]triazine; 2-(4-chloro-2,7-dimethylpyrazolo[1,5-a][1,3,5]triazin-8-yl)-5-methoxy-3-methylphenyl methyl ether | C16H17ClN4O2 | 详情 | 详情 | |
| (IX) | 38928 | (1R)-1-methylpropylamine; (2R)-2-butanamine | C4H11N | 详情 | 详情 |