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【结 构 式】 
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【分子编号】52509 【品名】4-cyano-N-[(2,2-dimethylcyclopentyl)methyl]benzamide 【CA登记号】 |
【 分 子 式 】C16H20N2O 【 分 子 量 】256.34768 【元素组成】C 74.97% H 7.86% N 10.93% O 6.24% |
合成路线1
该中间体在本合成路线中的序号：(V)Amine (III) was synthesized from 2,2-dimethylcyclopentanone (I) by treatment with tosylmethyl isocyanide, followed by reduction of the resultant nitrile (II) with LiAlH4. Condensation of 4-cyanobenzoic acid (IV) with amine (III) produced the corresponding amide (V). Subsequent addition of hydroxylamine to the cyano group of (V) gave rise to the hydroxyamidine (VI). The target oxadiazole derivative was then obtained by condensation of (VI) with 4,4,4-trifluorobutyric acid (VII), followed by cyclization under basic conditions. Separation of the enantiomers was carried out by chiral preparative HPLC.
| 【1】 LLoyd, J.; et al.; Design and synthesis of 4-substituted benzamides as potent, selective, and orally bioavailable IKS blockers. J Med Chem 2001, 44, 23, 3764. |
| 【2】 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) | 36897 | 4-cyanobenzoic acid；4-Carboxybenzonitrile;p-Carboxybenzonitrile | 619-65-8 | C8H5NO2 | 详情 | 详情 |
| (V) | 52509 | 4-cyano-N-[(2,2-dimethylcyclopentyl)methyl]benzamide | C16H20N2O | 详情 | 详情 | |
| (VI) | 52510 | 4-[amino(hydroxyimino)methyl]-N-[(2,2-dimethylcyclopentyl)methyl]benzamide | C16H23N3O2 | 详情 | 详情 | |
| (VII) | 14781 | 4,4,4-Trifluorobutyric acid | 406-93-9 | C4H5F3O2 | 详情 | 详情 |