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【结 构 式】 
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【药物名称】Mirfentanil hydrochloride, OHM-10579(free base), ANQ-3508 HCl, A-3508 hydrochloride 【化学名称】N-(1-Phenethyl-4-piperidinyl)-N-(2-pyrazinyl)furan-2-carboxamide hydrochloride 【CA登记号】119413-53-5, 117523-47-4 (free base), 118142-72-6 (oxalate salt) 【 分 子 式 】C22H25ClN4O2 【 分 子 量 】412.92315 |
【开发单位】Baxter (Originator) 【药理作用】ANALGESIC AND ANESTHETIC DRUGS, Analgesic Drugs, Opioid Analgesics, Opioid Agonists |
合成路线1
4-Amino-1-phenethylpiperidine (I) is stirred with chloropyrazine (II) and copper powder in phenyl ether at 170-175 C to obtain 1-phenethyl-4-[N-(pyrazinyl)amino]piperidine (III). Subsequent acylation of (III) with 2-furoyl chloride in 1,2-dichloroethane yields mirfentanil as the hydrochloride salt after cooling and filtration. Further purification is achieved by recrystallization from n-propanol.
| 【1】 Bagley, J.R.; Doorley, B.M.; Ossipov, M.H.; Knight, V.V.; Jerussi, T.P.; Benvenga, M.J.; Wilhelm, J.A.; Waters, S.J.; Spaulding, T.C.; Wynn, R.L.; Rudo, F.G.; Glass, P.S.A.; MIRFENTANIL HYDROCHLORIDE. Drugs Fut 1990, 15, 8, 798. |
| 【2】 Bagley, J.R.; Wynn, R.L.; Rudo, F.G.; Doorley, B.M.; Spender, H.K.; Spaulding, T.; New 4-(heteroanilido)-piperidines structurally related to the pure opioid agonist, fentanyl, with agonist and/or antagonist properties. J Med Chem 1989, 32, 3, 663-671. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 26093 | 2-Furoyl chloride | 527-69-5 | C5H3ClO2 | 详情 | 详情 | |
| (I) | 31167 | 1-phenethyl-4-piperidinylamine; 1-phenethyl-4-piperidinamine; N-(Phenethyl)-4-aminopiperidine | 51448-56-7 | C13H20N2 | 详情 | 详情 |
| (II) | 24075 | 2-chloropyrazine | 14508-49-7 | C4H3ClN2 | 详情 | 详情 |
| (III) | 31168 | N-(1-phenethyl-4-piperidinyl)-N-(2-pyrazinyl)amine; N-(1-phenethyl-4-piperidinyl)-2-pyrazinamine | C17H22N4 | 详情 | 详情 |