【结 构 式】 |
【药物名称】FUB-349(free base), VUF-5514 【化学名称】4-(4-Phenylbutyl)-1H-imidazole fumarate 【CA登记号】 【 分 子 式 】C17H20N2O4 【 分 子 量 】316.35995 |
【开发单位】Bioprojet (Originator) 【药理作用】Antiepileptic Drugs, Cognition Disorders, Treatment of, NEUROLOGIC DRUGS, PSYCHOPHARMACOLOGIC DRUGS, Sleep Disorders, Treatment of, Histamine H3 Receptor Antagonists |
合成路线1
The Wittig condensation of 1-tritylimidazole-4-carbaldehyde (I) with triphenyl(3-phenylpropyl)phosphonium bromide (II) and potassium tert-butoxide in THF gives 4-(4-phenyl-1(Z)-butenyl)-1-trityl-1H-imidazole (III), which is deprotected with 6N HCl in refluxing acetone yielding 4-(4-phenyl-1(Z)-butenyl)-1H-imidazole (IV). Finally, this compound is hydrogenated with H2 over Pd/C in methanol.
【1】 Stark, H.; Ligneau, X.; Arrang, J.-M.; Schwartz, J.-C.; Schunack, W.; General construction pattern of histamine H3-receptor antagonists: Change of a paradigm. Bioorg Med Chem Lett 1998, 8, 15, 2011. |
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) | 27712 | 1-trityl-1H-imidazole-4-carbaldehyde;1-Tritylimidazole-4-carboxaldehyde | 33016-47-6 | C23H18N2O | 详情 | 详情 |
(II) | 31037 | triphenyl(3-phenylpropyl)phosphonium bromide | 7484-37-9 | C27H26BrP | 详情 | 详情 |
(III) | 31038 | 4-[(Z)-4-phenyl-1-butenyl]-1-trityl-1H-imidazole | C32H28N2 | 详情 | 详情 | |
(IV) | 31039 | 4-[(Z)-4-phenyl-1-butenyl]-1H-imidazole | C13H14N2 | 详情 | 详情 |
Extended Information