Tecastemizole, Norastemizole, Soltara
诺阿斯米唑 诺拉斯三唑氢溴化物 Chemical Name: 1-(4-Fluorobenzyl)-2-(piperidin-4-ylamino)-1H-benzimidazole
CAS No. 75970-99-9, 75970-64-8 (diHBr salt)
项目整合开发状态: Discontinued
项目研究机构: Sepracor (Originator)
合成路线:The condensation of 2-chloro-1-(4-fluorobenzyl)-1H-benzimidazole (I) with methoxymethyl bromide (II) in toluene gives the benzimidazolium bromide (III),which is condensed with 4-aminopiperidine-1-carboxylic acid ethyl ester (IV) in hot toluene to yield the adduct (V).Finally,this compound is treated first with BBr3 in dichloromethane and then with HBr or HCl at 110 C to provide the target Norastemizole.
合成路线:The condensation of 2-chloro-1-(4-fluorobenzyl)-1H-benzimidazole (I) with 2-methoxyethoxymethyl bromide (II) in toluene gives the benzimidazolium bromide (III),which is condensed with 1-acetyl-4-aminopiperidine (IV) in hot toluene to yield the adduct (V).Finally,this compound is treated first with BBr3 in dichloromethane and then with HBr or HCl at 110 C to provide the target Norastemizole.
📌 参考资料/链接：
参考文献标题:Methods for synthesizing 2-substd.imidazoles
文献作者:Hong,Y.; Senanayake,C.H.; Bakale,R.P.(Sepracor Inc.)
参考来源:EP 0977740; JP 2001520658; US 5817823; WO 9846571
📄 详细内容
合成路线:Norastemizole can be obtained in the following way as shown in scheme:The synthesis is carried out by mild and selective palladium coupling of readily available 1-(4-fluorobenzyl)- 2-chlorobenzimidazole (I) with 4-aminopiperidine dihydrochloride (II) to obtain norastemizole in 84% isolated yield.The synthesis is highly selective and involves a one-step process.
参考文献标题:Norastemizole
文献作者:Senanayake,C.; Hong,Y.; Bakale,R.; Handley,D.A.
参考来源:Drugs Fut 1998,23(9),966
合成路线:Norastemizole can be obtained in the following way as shown in scheme:The synthesis is carried out by mild and selective palladium coupling of readily available 1-(4-fluorobenzyl)- 2-chlorobenzimidazole (I) with 4-aminopiperidine dihydrochloride (II) to obtain norastemizole in 84% isolated yield.The synthesis is highly selective and involves a one-step process.
参考文献标题:Palladium catalyzed amination of 2-chloro-1,3-azole derivatives: Mild entry to potent H1-antihistaminic norastemizole
文献作者:Wald,S.A.; Hong,Y.; Wilkinson,H.S.; Senanayake,C.H.; Tanoury,G.J.; Bakale,R.P.
参考来源:Tetrahedron Lett 1997,385607-10
合成路线:Norastemizole can be obtained in the following way as shown in scheme:The synthesis is carried out by mild and selective palladium coupling of readily available 1-(4-fluorobenzyl)- 2-chlorobenzimidazole (I) with 4-aminopiperidine dihydrochloride (II) to obtain norastemizole in 84% isolated yield.The synthesis is highly selective and involves a one-step process.
参考文献标题:Remarkably Selective Palladium-Catalyzed Amination Process: Rapid Assembly of Multiamino Based Structures
文献作者:Xiang,T.; Hong,Y.; Wald,S.A.; Tanoury,T.; Senanayake,C.H.; Vandenbossche,C.P.; Bakale,R.P.
参考来源:Tetrahedron Lett 1998,393121-4
产品链接: CAS No. 75970-99-9›› 产品链接: CAS No.75970-64-8››