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【结 构 式】 
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【药物名称】NBI-30545 【化学名称】N-[3-(2,4-Dimethoxyphenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-yl]-N-(2-methoxyethyl)-N-propylamine hydrochloride 【CA登记号】195054-99-0 (free base) 【 分 子 式 】C22H31ClN4O3 【 分 子 量 】434.97037 |
【开发单位】Janssen (Originator), Neurocrine Biosciences (Originator) 【药理作用】Antidepressants, Anxiolytics, Mood Disorders, Treatment of, PSYCHOPHARMACOLOGIC DRUGS, CRF1 Antagonists |
合成路线1
Aminopyrazole (I) was cyclized to pyrazolopyrimidine (III) by means of ethyl acetoacetate (II) in refluxing dioxan. Chlorination of (II) with POCl3 produced the corresponding chloro derivative (IV). This was then heated with an excess of amine (V) in a sealed vessel at 100 C to afford the target compound, which was isolated as the hydrochloride salt.
| 【1】 Chen, C.; Webb, T.R.; McCarthy, J.R.; Moran, T.J.; Wilcoxen, K.M. (Janssen Pharmaceutica NV; Neurocrine Biosciences Inc.); Pyrazolopyrimidines as CRF receptor antagonists. EP 0880523; JP 2000503661; WO 9729109 . |
| 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) | 27746 | 4-(2,4-dimethoxyphenyl)-3-methyl-1H-pyrazol-5-amine | C12H15N3O2 | 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) | 27747 | 3-(2,4-dimethoxyphenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-ol | C16H17N3O3 | 详情 | 详情 | |
| (IV) | 27748 | 2-(7-chloro-2,5-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)-5-methoxyphenyl methyl ether | C16H16ClN3O2 | 详情 | 详情 | |
| (V) | 27749 | N-(2-methoxyethyl)-1-propanamine | 43175-57-1 | C6H15NO | 详情 | 详情 |
Extended Information