E-6080
6-羟基-4,5,7-三甲基-2-(4-氨磺酰苯甲基氨基)苯并噻唑盐酸 4-[[[(6-羟基-4,5,7-三甲基-1,3-苯并噻唑-2-基)氨基]甲苯磺酰胺 Chemical Name: 6-Hydroxy-4,5,7-trimethyl-2-(4-sulfamoylbenzylamino)benzothiazole hydrochloride; 4-[[(6-Hydroxy-4,5,7-trimethyl-2-benzothiazolyl)amino]methyl]benzenesulfonamide hydrochloride
CAS No. 120164-49-0, 120165-51-7 (free base)
项目整合开发状态: Phase II
项目研究机构: Eisai (Originator)
合成路线:Reaction of 1-amino-4-methoxy-2,3,5-trimethylbenzene (I) with potassium thiocyanate and bromine in acetic acid gives 2-amino-6-methoxy-4,5,7-trimethylbenzothiazole (II),which is treated with 4-sulfamoylbenzoyl chloride [formed in situ from 4-sulfamoyl benzoic acid (III) and SOCl2],to afford 4-[N-(6-methoxy-4,5,7-trimethylbenzothiazol-2-yl)carbamoyl] benzenesulfonamide (IV).Compound (IV) is reduced with lithium aluminum hydride in tetrahydrofuran to yield 4-(6-methoxy-4,5,7-trimethylbenzothiazol-2-ylaminomethyl) benzenesulfonamide (V),which is finally demethylated with boron tribromide in methylene chloride.
📌 参考资料/链接：
参考文献标题:Benzothiazole deriv.,its use,and pharmaceutical compsns.comprising it
文献作者:Abe,S.; Miyamoto,M.; Tanaka,M.; Akasaka,K.; Hayashi,K.; Kawahara,T.; Katayama,T.; Sakuma,Y.; Suzuki,T.; Yamatsu,I.(Eisai Co.,Ltd.)
参考来源:EP 0295656; US 4929623
📄 详细内容
合成路线:Reaction of 1-amino-4-methoxy-2,3,5-trimethylbenzene (I) with potassium thiocyanate and bromine in acetic acid gives 2-amino-6-methoxy-4,5,7-trimethylbenzothiazole (II),which is treated with 4-sulfamoylbenzoyl chloride [formed in situ from 4-sulfamoyl benzoic acid (III) and SOCl2],to afford 4-[N-(6-methoxy-4,5,7-trimethylbenzothiazol-2-yl)carbamoyl] benzenesulfonamide (IV).Compound (IV) is reduced with lithium aluminum hydride in tetrahydrofuran to yield 4-(6-methoxy-4,5,7-trimethylbenzothiazol-2-ylaminomethyl) benzenesulfonamide (V),which is finally demethylated with boron tribromide in methylene chloride.
参考文献标题:E-6080
文献作者:Castar,J.; Prous,J.; Mealy,N.
参考来源:Drugs Fut 1993,18(11),991
产品链接: CAS No. 120164-49-0›› 产品链接: CAS No.120165-51-7››