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【结 构 式】 
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【分子编号】12757 【品名】2-Chloro-N,N-dimethyl-2-[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]acetamide 【CA登记号】 |
【 分 子 式 】C19H20ClN3O 【 分 子 量 】341.84012 【元素组成】C 66.76% H 5.9% Cl 10.37% N 12.29% O 4.68% |
合成路线1
该中间体在本合成路线中的序号：(VI)A new and industrially viable synthesis of zolpidem has been described: The cyclization of 2-amino-5-methylpyridine (I) with 4-methylphenacyl bromide (II) gives 6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridine (III), which is condensed with N,N-dimethylglyoxylamide (IV) to yield 2-hydroxy-N,N-dimethyl-2-[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyri din-3-yl]acetamide (V). The reaction of (V) with SOCl2 affords the corresponding chloroacetamide (VI), which is finally reduced to give zolpidem. This product is then converted into the hemitartrate salt. Via this synthesis, zolpidem is obtained in excellent yield and quality on an industrial scale.
| 【1】 Allen, J.; George, P.; Wick, A.; Mompon, B.; Depoortere, H.; Rossey, G.; Imidazopyridines: Towards novel hypnotic and anxiolytic drugs. Farmaco 1991, 46, 1, Suppl., 277-88. |
| 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) | 12752 | 5-Methyl-2-pyridinylamine; 2-Amino-5-methylpyridine; 5-Methyl-2-pyridinamine; 6-Amino-beta-picoline; 6-Amino-3-picoline | 1603-41-4 | C6H8N2 | 详情 | 详情 |
| (II) | 12753 | 2-Bromo-1-(4-methylphenyl)-1-ethanone | 619-41-0 | C9H9BrO | 详情 | 详情 |
| (III) | 12754 | 6-Methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridine | C15H14N2 | 详情 | 详情 | |
| (IV) | 12755 | N,N-Dimethyl-2-oxoacetamide | C4H7NO2 | 详情 | 详情 | |
| (V) | 12756 | 2-Hydroxy-N,N-dimethyl-2-[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]acetamide | C19H21N3O2 | 详情 | 详情 | |
| (VI) | 12757 | 2-Chloro-N,N-dimethyl-2-[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]acetamide | C19H20ClN3O | 详情 | 详情 |