Abecarnil, SH-524, ZK-112119
阿贝卡尔Chemical Name: 6-Benzyloxy-4-(methoxymethyl)-beta-carboline-3-carboxylic acid isopropyl ester; 6-Benzyloxy-4-(methoxymethyl)-9H-pyrido[3,4-b]indole-3-carboxylic acid isopropyl ester
CAS No. 111841-85-1
项目整合开发状态: Phase III
项目研究机构: Schering AG (Originator), Novo Nordisk (Licensee)
合成路线:The condensation of 5-benzyloxy-3-[1-(isopropylamino)-2-methoxyethyl]indole (I) with N-(4-methylbenzylidene)glycine isopropyl ester (II) by means of K2CO3 in hot DMF gives 2-amino-3-(5-benzyloxyindol-3-yl)-4-methoxybutyric acid isopropyl ester (III),which is cyclized with paraformaldehyde in refluxing xylene,yielding 6-benzyloxy-4-(methoxymethyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole - 3-carboxylic acid isopropyl ester (IV).Finally,this compound is dehydrogenated with tert-butyl hypochlorite and triethylamine in dichloromethane.
📌 参考资料/链接：
参考文献标题:5- or 6-Substd.-beta-carboline-3-carboxylic acid esters
文献作者:Biere,H.; Huth,A.; Rahtz,D.; Schmiechen,R.; Seidelmann,D.; Kehr,W.; Schneider,H.H.; Engelstoft,M.; Hansen,J.B.; Watjen,F.; Honore,T.(Schering AG)
参考来源:DE 3609699; EP 0239667; JP 1987221684; US 5414002; US 5700808
📄 详细内容
合成路线:The condensation of 5-benzyloxy-3-[1-(isopropylamino)-2-methoxyethyl]indole (I) with N-(4-methylbenzylidene)glycine isopropyl ester (II) by means of K2CO3 in hot DMF gives 2-amino-3-(5-benzyloxyindol-3-yl)-4-methoxybutyric acid isopropyl ester (III),which is cyclized with paraformaldehyde in refluxing xylene,yielding 6-benzyloxy-4-(methoxymethyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole - 3-carboxylic acid isopropyl ester (IV).Finally,this compound is dehydrogenated with tert-butyl hypochlorite and triethylamine in dichloromethane.
参考文献标题:Abecarnil
文献作者:Castar,J.; Pento,J.T.
参考来源:Drugs Fut 1993,18(5),411
产品链接: CAS No. 111841-85-1››