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【结 构 式】 
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【药物名称】 【化学名称】6-[1-[6-Cyano-2'-(trifluoromethyl)biphenyl-3-yl]-1-(1-methyl-1H-imidazol-5-yl)methoxymethyl]-2-(3-hydroxypiperidin-1-yl)pyridine-3-carbonitrile 【CA登记号】 【 分 子 式 】C31H27F3N6O2 【 分 子 量 】572.59504 |
【开发单位】Abbott (Originator) 【药理作用】ONCOLYTIC DRUGS, Farnesyl Transferase Inhibitors |
合成路线1
Suzuki coupling between 2-bromo-4-formylbenzonitrile (I) and 2-(trifluoromethyl)phenylboronic acid (II) affords the biphenyl aldehyde (III). The lithiated derivative of imidazole (IV) is then added to aldehyde (III), producing carbinol (V). Alkylation of (V) with the bromomethylpyridine (VI) by using Ag2O yields ether (VII). The chlorine atom of (VII) is finally displaced with 3-hydroxypiperidine (VIII) to provide the title compound.
| 【1】 Wang, G.T.; et al.; Lead optimization of imidazole-containing inhibitors of farnesyl transferase. 224th ACS Natl Meet (Aug 18 2002, Boston) 2002, Abst MEDI 130. |
| 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) | 58990 | 2-bromo-4-formylbenzonitrile | C8H4BrNO | 详情 | 详情 | |
| (II) | 53180 | 2-Trifluoromethylbenzeneboronic acid; 2-Trifluoromethylphenylboronic acid; o-Trifluoromethylphenylboronic acid | 1423-27-4 | C7H6BF3O2 | 详情 | 详情 |
| (III) | 58991 | 5-formyl-2'-(trifluoromethyl)[1,1'-biphenyl]-2-carbonitrile | C15H8F3NO | 详情 | 详情 | |
| (IV) | 58992 | 1-methyl-2-(triethylsilyl)-1H-imidazole | C10H20N2Si | 详情 | 详情 | |
| (V) | 58993 | 5-[hydroxy(1-methyl-1H-imidazol-5-yl)methyl]-2'-(trifluoromethyl)[1,1'-biphenyl]-2-carbonitrile | C19H14F3N3O | 详情 | 详情 | |
| (VI) | 58994 | 6-(bromomethyl)-2-chloronicotinonitrile | C7H4BrClN2 | 详情 | 详情 | |
| (VII) | 58995 | 2-chloro-6-{[[6-cyano-2'-(trifluoromethyl)[1,1'-biphenyl]-3-yl](1-methyl-1H-imidazol-5-yl)methoxy]methyl}nicotinonitrile | C26H17ClF3N5O | 详情 | 详情 | |
| (VIII) | 24255 | 3-piperidinol | 6859-99-0 | C5H11NO | 详情 | 详情 |
Extended Information