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【结 构 式】 
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【药物名称】DMP-904, SP-904 【化学名称】7-(1-Ethylpropylamino)-3-(4-methoxy-2-methylphenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidine 【CA登记号】202579-74-6 【 分 子 式 】C21H28N4O 【 分 子 量 】352.48351 |
【开发单位】Bristol-Myers Squibb (Originator) 【药理作用】Antidepressants, Anxiolytics, Mood Disorders, Treatment of, PSYCHOPHARMACOLOGIC DRUGS, CRF1 Antagonists |
合成路线1
The cyclization of 5-amino-4-(4-methoxy-2-methylphenyl)-3-methylpyrazole with ethyl acetoacetate (II) in refluxing acetic acid gives 7-hydroxy-3-(4-methoxy-2-methylphenyl)-5-methylpyrazolo[1,5-a]pyrimidine (III), which is treated with POCl3 and diethylaniline in refluxing toluene yielding the corresponding chloro derivative (IV). Finally, this compound is treated with pentyl-3-amine in DMSO at 150 C.
| 【1】 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) | 25921 | 4-(4-methoxy-2-methylphenyl)-3-methyl-1H-pyrazol-5-amine; 4-(4-methoxy-2-methylphenyl)-3-methyl-1H-pyrazol-5-ylamine | C12H15N3O | 详情 | 详情 | |
| (II) | 11819 | ethyl acetoacetate; ethyl 3-oxobutanoate；Acetoacetic ester;Ethyl beta-ketobutyrate;ethyl 3-oxobutyrate | 141-97-9 | C6H10O3 | 详情 | 详情 |
| (III) | 25922 | 3-(4-methoxy-2-methylphenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-ol | C16H17N3O2 | 详情 | 详情 | |
| (IV) | 25923 | 7-chloro-3-(4-methoxy-2-methylphenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidine; 4-(7-chloro-2,5-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methylphenyl methyl ether | C16H16ClN3O | 详情 | 详情 | |
| (V) | 25924 | 1-ethylpropylamine; 3-pentanamine | 616-24-0 | C5H13N | 详情 | 详情 |
Extended Information