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【结 构 式】 
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【药物名称】FR-188582 【化学名称】3-Chloro-5-[4-(methylsulfonyl)phenyl]-1-phenyl-1H-pyrazole 【CA登记号】189699-82-9 【 分 子 式 】C16H13ClN2O2S 【 分 子 量 】332.81121 |
【开发单位】Fujisawa (Originator) 【药理作用】Antiarthritic Drugs, TREATMENT OF MUSCULOSKELETAL & CONNECTIVE TISSUE DISEASES, Cyclooxygenase-2 Inhibitors |
合成路线1
The cyclization of phenylhydrazine (I) with 3-[4-(methylsulfanyl)phenyl]acrylonitrile (II) by means of NaOEt in refluxing ethanol gives the aminopyrazoline (III), which is dehydrogenated by means of MnO2 in dichloromethane to yield the 3-aminopyrazole (IV). The diazotation of (IV) with NaNO2 and HCl in water, followed by a treatment with Cu2Cl2, affords the 3-chloropyrazole (V), which is finally oxidized to the target sulfone by means of MCPBA in dichloromethane.
| 【1】 Matsuo, M.; Okumura, K.; Ogino, T.; Nakamura, K.; Nishimura, H.; Harada, K.; Hotta, Y.; Tsuji, K. (Fujisawa Pharmaceutical Co., Ltd.); 1,3,5-Trisubstd. pyrazoles for treatment of inflammation. EP 0856000; JP 1999513403; WO 9713755 . |
| 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) | 11818 | Phenyl hydrazine; 1-Phenylhydrazine | 100-63-0 | C6H8N2 | 详情 | 详情 |
| (II) | 52011 | (E)-3-[4-(methylsulfanyl)phenyl]-2-propenenitrile | C10H9NS | 详情 | 详情 | |
| (III) | 52012 | 5-[4-(methylsulfanyl)phenyl]-1-phenyl-4,5-dihydro-1H-pyrazol-3-amine; 5-[4-(methylsulfanyl)phenyl]-1-phenyl-4,5-dihydro-1H-pyrazol-3-ylamine | C16H17N3S | 详情 | 详情 | |
| (IV) | 52013 | 5-[4-(methylsulfanyl)phenyl]-1-phenyl-1H-pyrazol-3-ylamine; 5-[4-(methylsulfanyl)phenyl]-1-phenyl-1H-pyrazol-3-amine | C16H15N3S | 详情 | 详情 | |
| (V) | 52014 | 4-(3-chloro-1-phenyl-1H-pyrazol-5-yl)phenyl methyl sulfide; 3-chloro-5-[4-(methylsulfanyl)phenyl]-1-phenyl-1H-pyrazole | C16H13ClN2S | 详情 | 详情 |