Tiracizine hydrochloride, GS-015, AWD-19-166, Bonnecor
[5-[(二甲氨基)乙酰基]-10,11-二氢-5H-二苯并[B,F]氮杂革-3-基]氨基甲酸乙酯单盐酸盐 替拉西秦 Chemical Name: 3-Carbethoxyamino-5-dimethylaminoacetyl-10,11-dihydro-5H-dibenz[b,f]azepine monohydrochloride; 5-(N,N-Dimethylglycyl)-10,11-dihydro-5H-dibenz[b,f]azepine-3-carbamic acid ethyl ester monohydrochloride
CAS No. 78816-67-8, 83275-56-3 (free base)
项目整合开发状态: Launched-1990
项目研究机构: AWD.pharma (Originator)
合成路线:Reaction of 3-amino-5-acetyl-10,11-dihydro-5H-dibenz[b,f]azepine (I) with potassium hydroxide in n-propanol yields 3-amino-10,11-dihydro-5H-dibenz[b,f]azepine (II),which reacts with ethyl chloroformate to give 3-carbethoxyamino-10,11-dihydro-5H-dibenz[b,f]azepine (III).Reaction of (III) with chloroacetylchloride yields 3-carbethoxyamino-5-chloroacetyl-10,11-dihydro-5H-dibenz[b,f]azepine (IV),which is then reacted with dimethylamine to give 3-carbethoxyamino-5-dimethylaminoacetyl-10,11-dihydro-5H-dibenz[b,f] azepine (tiracizine) (V),with m.p.135-7 C.Tiracizine hydrochloride is obtained by reaction of the base with hydrochloric acid in isopropanol.
📌 参考资料/链接：
参考文献标题:Process for the preparation of novel 10,11-dihydro-5H-dibenz[b,f]azepines and their salts
文献作者:Carstens,E.; Wunderlich,H.; Stark,A.; Kayerina,N.; Senova,S.P.; Lystkovzev,V.V.; Jermakova,S.I.; Grizenko,A.N.; Skoldinov,A.P.(Arzneimittelwerk Dresden GmbH)
参考来源:DE 3040085
📄 详细内容
合成路线:Reaction of 3-amino-5-acetyl-10,11-dihydro-5H-dibenz[b,f]azepine (I) with potassium hydroxide in n-propanol yields 3-amino-10,11-dihydro-5H-dibenz[b,f]azepine (II),which reacts with ethyl chloroformate to give 3-carbethoxyamino-10,11-dihydro-5H-dibenz[b,f]azepine (III).Reaction of (III) with chloroacetylchloride yields 3-carbethoxyamino-5-chloroacetyl-10,11-dihydro-5H-dibenz[b,f]azepine (IV),which is then reacted with dimethylamine to give 3-carbethoxyamino-5-dimethylaminoacetyl-10,11-dihydro-5H-dibenz[b,f] azepine (tiracizine) (V),with m.p.135-7 C.Tiracizine hydrochloride is obtained by reaction of the base with hydrochloric acid in isopropanol.
参考文献标题:Tiracizine Hydrochloride
文献作者:Rejholec,V.
参考来源:Drugs Fut 1991,16(9),818
合成路线:Reaction of 3-amino-5-acetyl-10,11-dihydro-5H-dibenz[b,f]azepine (I) with potassium hydroxide in n-propanol yields 3-amino-10,11-dihydro-5H-dibenz[b,f]azepine (II),which reacts with ethyl chloroformate to give 3-carbethoxyamino-10,11-dihydro-5H-dibenz[b,f]azepine (III).Reaction of (III) with chloroacetylchloride yields 3-carbethoxyamino-5-chloroacetyl-10,11-dihydro-5H-dibenz[b,f]azepine (IV),which is then reacted with dimethylamine to give 3-carbethoxyamino-5-dimethylaminoacetyl-10,11-dihydro-5H-dibenz[b,f] azepine (tiracizine) (V),with m.p.135-7 C.Tiracizine hydrochloride is obtained by reaction of the base with hydrochloric acid in isopropanol.
参考文献标题:Synthesis of new antiarrhythmic compound
文献作者:Wunderlich,H.; Stark,A.; Loman,D.; Skoldinov,A.P.; Gritsenko,A.N.; Carstens,E.
参考来源:Bonnecor.Khim Farm Zh SSSR 1990,24(12),51
产品链接: CAS No. 78816-67-8›› 产品链接: CAS No.83275-56-3››