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【结 构 式】 
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【药物名称】S-1389, 711389-S 【化学名称】1-[2,5-Dichloro-6-[1-(1H-imidazol-1-yl)ethenyl]phenoxy]-3-[(1-methylethyl)amino]-2-propanol hydrochloride 【CA登记号】90821-25-3 ((R)-(+)-isomer), 90821-27-5 ((S)-(-)-isomer), 90742-91-9 (racemate), 90742-90-8 (racemic free base) 【 分 子 式 】C17H22Cl3N3O2 【 分 子 量 】406.74279 |
【开发单位】Shionogi (Originator) 【药理作用】Antiarrhythmic Drugs, CARDIOVASCULAR DRUGS |
合成路线1
This 1-vinylimidazole compound (II) is obtained by reaction of N,N'-thionyldiimidazole (A) with 2-hydroxy-3,6-dichloroacetophenone (I) in dichloro-methane. Treatment of (II) with epibromohydrin (B) in DMF in the presence of NaH gives the epoxy compound (III), which is then treated with isopropylamine (C) to obtain the propanolamine compound (IV). The hydrochloride can be prepared by treatment of the free base (IV) with one molar equivalent of HCl in AcOEt.
| 【1】 Kida, S.; Ueda, M.; Kimoto, S.; Haruna, M.; Matsumoto, H.; Takahashi, K.; Ogata, M.; Synthesis and antiarrhythmic activity of new 1-[1-[2-[3-(alkylamino)-2-hydroxypropoxy]phenyl]vinyl]-1H-imidazoles and related compounds. J Med Chem 1984, 27, 9, 1142. |
| 【2】 Ueda, M.; 711389-S. Drugs Fut 1985, 10, 6, 472. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 29655 | 1-(1H-imidazol-1-ylsulfinyl)-1H-imidazole | C6H6N4OS | 详情 | 详情 | |
| (B) | 29679 | 2-(bromomethyl)oxirane | 3132-64-7 | C3H5BrO | 详情 | 详情 |
| (I) | 29677 | 1-(3,6-dichloro-2-hydroxyphenyl)-1-ethanone | C8H6Cl2O2 | 详情 | 详情 | |
| (II) | 29678 | 3,6-dichloro-2-[1-(1H-imidazol-1-yl)vinyl]phenol | C11H8Cl2N2O | 详情 | 详情 | |
| (III) | 29680 | 3,6-dichloro-2-[1-(1H-imidazol-1-yl)vinyl]phenyl 2-oxiranylmethyl ether; 1-[1-[3,6-dichloro-2-(2-oxiranylmethoxy)phenyl]vinyl]-1H-imidazole | C14H12Cl2N2O2 | 详情 | 详情 | |
| (IV) | 29681 | 1-[3,6-dichloro-2-[1-(1H-imidazol-1-yl)vinyl]phenoxy]-3-(isopropylamino)-2-propanol | C17H21Cl2N3O2 | 详情 | 详情 | |
| (C) | 23933 | 2-Propanamine; Isopropylamine | 75-31-0 | C3H9N | 详情 | 详情 |