YM17E

Chemical Name: 1,3-Bis[1-cycloheptyl-3-[4-(dimethylamino)phenyl]ureidomethyl]benzene dihydrochloride; 1,1'-(1,3-Phenylene)bismethylenebis[1-cycloheptyl-3-[4-(dimethylamino)phenyl]urea] dihydrochloride
CAS No. 124884-99-7, 124900-72-7 (free base)
项目整合开发状态: Phase I
项目研究机构: Yamanouchi (Originator)
合成路线:Reaction of isophthaloyl dichloride (I) with cycloheptylamine (II) in the presence of triethylamine in dichloromethane gives N,N'-dicycloheptylisophthalimide (III),which is reduced with sodium bis(2-methoxyethoxy)aluminum hydride in toluene to yield 1,3-bis(cycloheptylaminomethyl)benzene (IV).Compound (IV) is treated with p-nitrophenylisocyanate (V) to afford 1,3-bis[1-cycloheptyl-3-(4-nitrophenyl)ureidomethyl]benzene (VI),which is reduced with hydrogen in the presence of palladium over charcoal to give 1,3-bis[1-cycloheptyl-3-(4-aminophenyl)ureidomethyl]benzene (VII).Finally,compound (VII) is treated with aqueous formaldehyde and hydrogen in the presence of platinum oxide in ethanol,followed by addition of hydrochloric acid in ethanol.
📌 参考资料/链接:
参考文献标题:Diurea derivatives useful as medicaments and processes for the preparation thereof
文献作者:Ito,N.; Yasunaga,T.; Iizumi,Y.; Araki,T.(Yamanouchi Pharmaceutical Co.,Ltd.)
参考来源:AU 8928669; EP 0325397; JP 1990117651; US 5091419; US 5166429; US 5384425

📄 详细内容


合成路线:Reaction of isophthaloyl dichloride (I) with cycloheptylamine (II) in the presence of triethylamine in dichloromethane gives N,N'-dicycloheptylisophthalimide (III),which is reduced with sodium bis(2-methoxyethoxy)aluminum hydride in toluene to yield 1,3-bis(cycloheptylaminomethyl)benzene (IV).Compound (IV) is treated with p-nitrophenylisocyanate (V) to afford 1,3-bis[1-cycloheptyl-3-(4-nitrophenyl)ureidomethyl]benzene (VI),which is reduced with hydrogen in the presence of palladium over charcoal to give 1,3-bis[1-cycloheptyl-3-(4-aminophenyl)ureidomethyl]benzene (VII).Finally,compound (VII) is treated with aqueous formaldehyde and hydrogen in the presence of platinum oxide in ethanol,followed by addition of hydrochloric acid in ethanol.

参考文献标题:Synthesis and hypocholesterolemic activity of phenylene and pyridylene diurea derivatives as ACAT inhibitors
文献作者:Iizumi,Y.; Ohhata,I.; Iwaoka,K.; Matsuda,K.; Ito,N.; Yasunaga,T.; Araki,T.
参考来源:202nd ACS Natl Meet (Aug 25-30,New York) 1991,Abst MEDI 109


合成路线:Reaction of isophthaloyl dichloride (I) with cycloheptylamine (II) in the presence of triethylamine in dichloromethane gives N,N'-dicycloheptylisophthalimide (III),which is reduced with sodium bis(2-methoxyethoxy)aluminum hydride in toluene to yield 1,3-bis(cycloheptylaminomethyl)benzene (IV).Compound (IV) is treated with p-nitrophenylisocyanate (V) to afford 1,3-bis[1-cycloheptyl-3-(4-nitrophenyl)ureidomethyl]benzene (VI),which is reduced with hydrogen in the presence of palladium over charcoal to give 1,3-bis[1-cycloheptyl-3-(4-aminophenyl)ureidomethyl]benzene (VII).Finally,compound (VII) is treated with aqueous formaldehyde and hydrogen in the presence of platinum oxide in ethanol,followed by addition of hydrochloric acid in ethanol.

参考文献标题:Synthesis and activity of a novel phenylenediurea derivative with hypolipidemic and antiatherosclerotic activity
文献作者:Yasunaga,T.; Araki,T.; Iwaoka,K.; Iizumi,Y.; Ohata,I.; Matsuda,K.; Ito,N.
参考来源:111th Annu Meet Pharmaceut Soc Jpn (March 28-30,Tokyo) 1991,Abst 29V 3-040.


合成路线:Reaction of isophthaloyl dichloride (I) with cycloheptylamine (II) in the presence of triethylamine in dichloromethane gives N,N'-dicycloheptylisophthalimide (III),which is reduced with sodium bis(2-methoxyethoxy)aluminum hydride in toluene to yield 1,3-bis(cycloheptylaminomethyl)benzene (IV).Compound (IV) is treated with p-nitrophenylisocyanate (V) to afford 1,3-bis[1-cycloheptyl-3-(4-nitrophenyl)ureidomethyl]benzene (VI),which is reduced with hydrogen in the presence of palladium over charcoal to give 1,3-bis[1-cycloheptyl-3-(4-aminophenyl)ureidomethyl]benzene (VII).Finally,compound (VII) is treated with aqueous formaldehyde and hydrogen in the presence of platinum oxide in ethanol,followed by addition of hydrochloric acid in ethanol.
参考文献标题:YM17E
文献作者:Graul,A.; Castar,J.; Prous,J.
参考来源:Drugs Fut 1993,18(9),813


产品链接: CAS No. 124884-99-7››

产品链接: CAS No.124900-72-7››