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【结 构 式】 
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【药物名称】OT-7100 【化学名称】5-Butyl-7-(3,4,5-trimethoxybenzamido)pyrazolo[1,5-a]pyrimidine 【CA登记号】174858-27-6 【 分 子 式 】C20H24N4O4 【 分 子 量 】384.43868 |
【开发单位】Otsuka (Originator) 【药理作用】ANALGESIC AND ANESTHETIC DRUGS, Analgesic Drugs, Non-Opioid Analgesics, Tachykinin NK1 Antagonists |
合成路线1
5-Butyl-7-hydroxypyrazolo[1,5-a]pyrimidine (III) was prepared by condensation of 3-aminopyrazole (I) with methyl 3-oxoheptanoate (II) in refluxing toluene. Treatment of (III) with POCl3 in the presence of Et3N furnished the 7-chloro derivative (IV), which was then heated with aqueous ammonia in a sealed tube to afford the amino pyrazolopyrimidine (V). Finally, acylation of amine (V) with 3,4,5-trimethoxybenzoyl chloride (VI) led to the title amide.
| 【1】 Shoji, Y.; Yasuda, T.; Inoue, M.; Okamura, T.; Hashimoto, K.; Ohara, M. (Otsuka Pharmaceutical Co., Ltd.); Pyrazolo[1,5-a]pyrimidine deriv.. EP 0714898; JP 1996310951; JP 1996311068; US 5707997; WO 9535298 . |
| 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) | 56012 | 1H-pyrazol-5-amine; 1H-pyrazol-5-ylamine | 916420-28-5 | C3H5N3 | 详情 | 详情 |
| (II) | 56013 | 3-Ketoheptanoic acid methyl ester; 3-Oxokenanthic acid mehyl ester; Methyl 3-oxoheptanoate | 39815-78-6 | C8H14O3 | 详情 | 详情 |
| (III) | 56014 | 5-butylpyrazolo[1,5-a]pyrimidin-7-ol | C10H13N3O | 详情 | 详情 | |
| (IV) | 56015 | 5-butyl-7-chloropyrazolo[1,5-a]pyrimidine | C10H12ClN3 | 详情 | 详情 | |
| (V) | 56016 | 5-butylpyrazolo[1,5-a]pyrimidin-7-amine; 5-butylpyrazolo[1,5-a]pyrimidin-7-ylamine | C10H14N4 | 详情 | 详情 | |
| (VI) | 13571 | 3,4,5Ttrimethoxybenzoyl chloride | 4521-61-3 | C10H11ClO4 | 详情 | 详情 |