KW-5805
Chemical Name: 5-[2-(Diethylamino)ethylamino]-5,11-dihydro[1]benzoxepino[3,4-b]pyridine
CAS No. 95968-63-1, 95968-62-0 (hydrochloride)
项目整合开发状态: Phase II
项目研究机构: Kyowa Hakko (Originator)
合成路线:The reaction of phenol (I) with ethyl 4-chloroacetoacetate (II) by means of KOH in DMSO gives ethyl 4 phenoxyacetoacetate (III),which by treatment with NH3 is converted into ethyl 3-amino-4-phenoxycrotonate (IV).The cyclization of (IV) with propargyl aldehyde (V) in hot toluene affords ethyl 2-(phenoxymethyl)nicotinate (VI),which is cyclized again by means of polyphosphoric acid (PPA) to yield 5,11-dihydro[1]benzoxepino[3,4-b)pyridin-5-one (VII).The reduction of (VII) with NaBH4 in ethanol gives the corresponding alcohol (VIII),which is finally condensed with N,N-diethylethylene diamine (IX) by means of SOCl2 in dichloromethane.
📌 参考资料/链接：
参考文献标题:Benzepino[3,4-b]pyridine derivs.
文献作者:Kumazawa,T.; Oiji,Y.; Shuto,K.; Tanaka,H.(Kyowa Hakko Kogyo Co.,Ltd.)
参考来源:EP 0129879; JP 1985006690; JP 1985078985; JP 1985089419; US 4547496
📄 详细内容
合成路线:The reaction of phenol (I) with ethyl 4-chloroacetoacetate (II) by means of KOH in DMSO gives ethyl 4 phenoxyacetoacetate (III),which by treatment with NH3 is converted into ethyl 3-amino-4-phenoxycrotonate (IV).The cyclization of (IV) with propargyl aldehyde (V) in hot toluene affords ethyl 2-(phenoxymethyl)nicotinate (VI),which is cyclized again by means of polyphosphoric acid (PPA) to yield 5,11-dihydro[1]benzoxepino[3,4-b)pyridin-5-one (VII).The reduction of (VII) with NaBH4 in ethanol gives the corresponding alcohol (VIII),which is finally condensed with N,N-diethylethylene diamine (IX) by means of SOCl2 in dichloromethane.
参考文献标题:KW-5805
文献作者:Castar,J.; Prous,J.
参考来源:Drugs Fut 1988,13(11),954
合成路线:The reaction of phenol (I) with ethyl 4-chloroacetoacetate (II) by means of KOH in DMSO gives ethyl 4 phenoxyacetoacetate (III),which by treatment with NH3 is converted into ethyl 3-amino-4-phenoxycrotonate (IV).The cyclization of (IV) with propargyl aldehyde (V) in hot toluene affords ethyl 2-(phenoxymethyl)nicotinate (VI),which is cyclized again by means of polyphosphoric acid (PPA) to yield 5,11-dihydro[1]benzoxepino[3,4-b)pyridin-5-one (VII).The reduction of (VII) with NaBH4 in ethanol gives the corresponding alcohol (VIII),which is finally condensed with N,N-diethylethylene diamine (IX) by means of SOCl2 in dichloromethane.
参考文献标题:Synthesis and antiulcer activity of 5,11-dihydro[1]benzoxepino[3,4-b]pyridines.
文献作者:Kumazawa,T.; Harakawa,H.; Obase,H.; Oijo,Y.; Tanaka,H.; Shuto,K.; Ishii,A.; Oka,T.; Nakamizo,N.
参考来源:J Med Chem 1988,31(4),779
产品链接: CAS No.95968-62-0››