Venritidine hydrochloride, D-16637
文立替丁Chemical Name: (?-(Z)-N-Methyl-2-nitro-N'-[2-[[5-[(tricyclo[2.2.1.0(2,6)]hept-3-ylamino)methyl]furfuryl]thio]ethyl]-1,1-ethenediamine
CAS No. 93064-63-2 (free base)
项目整合开发状态: Preclinical
项目研究机构: Degussa (Originator)
合成路线:The Mannich reaction of tricyclo[2.2.1.0(2,6)]hept-3-ylamine hydrochloride (I) with 2-furanylmethanol (II) and paraformaldehyde (III) in ethanol gives 5-(tricyclo[2.2.1.0(2,6)]hept-3-ylamino)methyl-2-furanyl methanol (IV).The reaction of compound (IV) with 2 mercaptoethylamine (V) by means of concentrated HCl affords 2 [[[5-[(tricyclo[2.2.1.0(2,6)]hept-3-yl-amino(methyl]-2-furanyl]methyl]thio]etheneamine (VI),which is converted with 1 1-bis(methylthio)-2-nitroethene (VII) in isopropyl alcohol by heating at 70 C to N-[2-[[[5 [(tricyclo[2.2.1.O(2,6)]hept-3-ylamino)methyl]-2-furanyl]methyl]thio]ethyl]-1-(methylthio)-2-nitroetheneamine (VIII).Compound (VIII) is then treated with excess methylamine in ethanol at 0 C,followed by treatment with ethereal HCl to give the desired-N-[2-[[[5 [(tricyclo[2.2.1.0(2,6)]hept-3-ylamino)methyl]-2 furanyl]methyl]thio]ethyl] N'- methyl-2-nitro-1,1-ethenediaminehydrochloride.
📌 参考资料/链接：
参考文献标题:Novel ethenediamine and guanidine derivatives
文献作者:Emig,P.; et al.(Degussa-H黮s AG)
参考来源:DE 3343884
📄 详细内容
合成路线:The Mannich reaction of tricyclo[2.2.1.0(2,6)]hept-3-ylamine hydrochloride (I) with 2-furanylmethanol (II) and paraformaldehyde (III) in ethanol gives 5-(tricyclo[2.2.1.0(2,6)]hept-3-ylamino)methyl-2-furanyl methanol (IV).The reaction of compound (IV) with 2 mercaptoethylamine (V) by means of concentrated HCl affords 2 [[[5-[(tricyclo[2.2.1.0(2,6)]hept-3-yl-amino(methyl]-2-furanyl]methyl]thio]etheneamine (VI),which is converted with 1 1-bis(methylthio)-2-nitroethene (VII) in isopropyl alcohol by heating at 70 C to N-[2-[[[5 [(tricyclo[2.2.1.O(2,6)]hept-3-ylamino)methyl]-2-furanyl]methyl]thio]ethyl]-1-(methylthio)-2-nitroetheneamine (VIII).Compound (VIII) is then treated with excess methylamine in ethanol at 0 C,followed by treatment with ethereal HCl to give the desired-N-[2-[[[5 [(tricyclo[2.2.1.0(2,6)]hept-3-ylamino)methyl]-2 furanyl]methyl]thio]ethyl] N'- methyl-2-nitro-1,1-ethenediaminehydrochloride.
参考文献标题:D-16637
文献作者:Castar,J.; Prous,J.
参考来源:Drugs Fut 1986,11(1),14
产品链接: CAS No. 93064-63-2››