新产品编号:797837
Chemical Name: N-(4,5-Dihydro-1H-imidazol-2-ylmethyl)-N-[5-methoxy-2-(methylsulfonyl)phenyl]amine fumarate
CAS No. 305809-61-4, 305809-60-3 (free base)
项目整合开发状态: Biological Testing
项目研究机构: GlaxoSmithKline (Originator)
合成路线:2-(Methylthio)aniline (I) was alkylated with 2-(chloromethyl)-2-imidazoline hydrochloride (II) in phenol at 120 C to afford the condensation product (III).Subsequent oxidation of the thioether functionality of (III) with m-chloroperbenzoic acid gave rise to the target sulfone.
合成路线:5-Methoxy-2-methylbenzothiazole (I) is hydrolyzed by NaOH in ethylene glycol to furnish 2-amino-4-methoxythiophenol (II),which is further alkylated with iodomethane and potassium tert-butoxide,yielding thioether (III).Condensation of aniline (III) with 2-(chloromethyl)imidazoline (IV) in the presence of phenol provides (V).After oxidation of sulfide (V) to the corresponding sulfone by means of m-chloroperbenzoic acid,the title compound is isolated as its fumarate salt (1,2).
📌 参考资料/链接：
参考文献标题:Imidazoline derivs.as alpha-1A adrenoceptor ligands
文献作者:Hodson,S.J.; Navas,F.III; Bishop,M.J.; Bigham,E.C.; Garrison,D.T.; Drewry,D.H.; Speake,J.D.(Glaxo Group Ltd.)
参考来源:WO 0066563
📄 详细内容
合成路线:5-Methoxy-2-methylbenzothiazole (I) is hydrolyzed by NaOH in ethylene glycol to furnish 2-amino-4-methoxythiophenol (II),which is further alkylated with iodomethane and potassium tert-butoxide,yielding thioether (III).Condensation of aniline (III) with 2-(chloromethyl)imidazoline (IV) in the presence of phenol provides (V).After oxidation of sulfide (V) to the corresponding sulfone by means of m-chloroperbenzoic acid,the title compound is isolated as its fumarate salt (1,2).
参考文献标题:2-(Anilinomethyl)imidazolines as alpha1 adrenergic receptor agonists: The discovery of alpha1a subtype selective 2'-alkylsulfonyl-substituted analogues
文献作者:Hodson,S.J.; Bishop,M.J.; Speake,J.D.; Navas,F.III; Garrison,D.T.; Bigham,E.C.; Saussy,D.L.Jr.; Liacos,J.A.; Irving,P.E.; Gobel,M.J.; Sherman,B.W.
参考来源:J Med Chem 2002,45(11),2229