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【结 构 式】 
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【药物名称】BMS-208782 【化学名称】(S)-4-(3-Butyl-1,2,4-oxadiazol-5-yl)-N-(2,2-dimethylcyclopentylmethyl)benzamide 【CA登记号】212380-82-0 ((-)-enantiomer), 212380-81-9 ((+)-enantiomer) 【 分 子 式 】C21H29N3O2 【 分 子 量 】355.48418 |
【开发单位】Bristol-Myers Squibb (Originator) 【药理作用】Antiarrhythmic Drugs, CARDIOVASCULAR DRUGS, Voltage-Gated K(V) Channel Blockers |
合成路线1
Treatment of 2,2-dimethylcyclopentanone (I) with tosylmethyl isocyanide and potassium tert-butoxide produced nitrile (II), which was reduced to amine (III) employing LiAlH4 in THF. Coupling of amine (III) with mono-methyl terephthalate (IV) by means of EDC and HOBt gave amide (V). The target oxadiazole system was then obtained by condensation of (V) with N-hydroxypentamidine (VI) in the presence of NaH, and the (S)-enantiomer was isolated by using chiral HPLC.
| 【1】 Poss, M.A.; Lloyd, J.; Rovnyak, G.C.; Caulfield, T.J.; Atwal, K.S.; Stein, P.D.; Ahmad, S. (Bristol-Myers Squibb Co.); Benzoic acid derivs. and related cpds. as antiarrhythmic agents. WO 9837068 . |
| 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) | 43358 | 2,2-dimethylcyclopentanone | C7H12O | 详情 | 详情 | |
| (II) | 43359 | 2,2-dimethylcyclopentanecarbonitrile | C8H13N | 详情 | 详情 | |
| (III) | 43360 | (2,2-dimethylcyclopentyl)methylamine; (2,2-dimethylcyclopentyl)methanamine | C8H17N | 详情 | 详情 | |
| (IV) | 43361 | 4-(methoxycarbonyl)benzoic acid | 1679-64-7 | C9H8O4 | 详情 | 详情 |
| (V) | 43362 | methyl 4-([[(2,2-dimethylcyclopentyl)methyl]amino]carbonyl)benzoate | C17H23NO3 | 详情 | 详情 | |
| (VI) | 43363 | N'-hydroxypentanimidamide | C5H12N2O | 详情 | 详情 |