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【结 构 式】 
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【药物名称】Pentisomide, Penticainide, ME-3202, CM-7857 【化学名称】2-[2-(Diisopropylamino)ethyl]-4-methyl-2-(2-pyridyl)pentanamide 【CA登记号】78833-03-1, 96513-83-6 (racemate) 【 分 子 式 】C19H33N3O 【 分 子 量 】319.49436 |
【开发单位】Sanofi-synthélabo (Originator), Meiji Seika (Licensee) 【药理作用】Antiarrhythmic Drugs, CARDIOVASCULAR DRUGS |
合成路线1
The condensation of 2-pyridylacetonitrile (I) with isobutyraldehyde (II) in refluxing benzene gives 4-methyl-2-(2-pyridyl)-2-pentenenitrile (III), which is hydrogenated over Pd/C yielding 4-methyl-2-(2-pyridyl)pentanenitrile (IV). The alkylation of (IV) with 2-(diisopropylamino)ethyl chloride (A) in DMF affords 2-[2-(diisopropylamino)ethyl]-4-methyl-2-(2-pyridyl)pentanenitrile (V), which is then hydrolyzed in concentrated sulfuric acid.
| 【1】 EP 0027412 . |
| 【2】 Gagnol, J.P.; Gautier, P.; Bernhart, C.A.; Serre, M.; Condamine, C.; Demarne, H.; Roncucci, R.; Synthesis and antiarrhythmic activity of new (dialkylamino)alkylpyridylacetamides. J Med Chem 1983, 26, 3, 451. |
| 【3】 Blancafort, P.; Castaner, J.; Serradell, M.N.; CM-7857. Drugs Fut 1983, 8, 12, 1016. |
| 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) | 36182 | N-(2-chloroethyl)-N-isopropyl-2-propanamine; N-(2-chloroethyl)-N,N-diisopropylamine | C8H18ClN | 详情 | 详情 | |
| (I) | 36179 | 2-(2-pyridinyl)acetonitrile | C7H6N2 | 详情 | 详情 | |
| (II) | 13226 | 2-Methylpropanal; Isobutyraldehyde | 78-84-2 | C4H8O | 详情 | 详情 |
| (III) | 36180 | (E)-4-methyl-2-(2-pyridinyl)-2-pentenenitrile | C11H12N2 | 详情 | 详情 | |
| (IV) | 36181 | 4-methyl-2-(2-pyridinyl)pentanenitrile | C11H14N2 | 详情 | 详情 | |
| (V) | 36183 | 2-[2-(diisopropylamino)ethyl]-4-methyl-2-(2-pyridinyl)pentanenitrile | C19H31N3 | 详情 | 详情 |