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【结 构 式】 
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【药物名称】Org-25543 【化学名称】4-Benzyloxy-N-[1-(dimethylamino)cyclopentylmethyl]-3,5-dimethoxybenzamide 【CA登记号】 【 分 子 式 】C24H32N2O4 【 分 子 量 】412.53364 |
【开发单位】Organon (Originator) 【药理作用】ANALGESIC AND ANESTHETIC DRUGS, Analgesic Drugs, Neuropathic Pain, Treatment of, GlyT-2 Inhibitors |
合成路线1
Aminonitrile (II) was prepared by Strecker reaction of cyclopentanone (I) with potassium cyanide and dimethylamine hydrochloride. Subsequent reduction of (II) with alane, generated in situ from LiAlH4 and H2SO4, produced diamine (III).
| 【1】 Caulfield, W.L.; et al.; The first potent and selective inhibitors of the glycine transporter type 2. J Med Chem 2001, 44, 17, 2679. |
合成路线2
Alkylation of methyl 4-hydroxy-3,5-dimethoxybenzoate (IV) with benzyl bromide afforded the corresponding 4-benzyloxy derivative (V). After basic hydrolysis of the methyl ester group of (V), the resultant carboxylic acid (VI) was converted to acid chloride (VII) using thionyl chloride in refluxing toluene. Then, acylation of diamine (III) with acid chloride (VII) afforded the title amide.
| 【1】 Caulfield, W.L.; et al.; The first potent and selective inhibitors of the glycine transporter type 2. J Med Chem 2001, 44, 17, 2679. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (III) | 51023 | 1-(aminomethyl)-N,N-dimethylcyclopentanamine; N-[1-(aminomethyl)cyclopentyl]-N,N-dimethylamine | C8H18N2 | 详情 | 详情 | |
| (IV) | 51024 | Methyl-3,5-dimethoxy-4-hydroxybenzoate | C10H12O5 | 详情 | 详情 | |
| (V) | 51025 | methyl 4-(benzyloxy)-3,5-dimethoxybenzoate | C17H18O5 | 详情 | 详情 | |
| (VI) | 51026 | 4-(benzyloxy)-3,5-dimethoxybenzoic acid | C16H16O5 | 详情 | 详情 | |
| (VII) | 51027 | 4-(benzyloxy)-3,5-dimethoxybenzoyl chloride | C16H15ClO4 | 详情 | 详情 |