Rocastine fumarate, AHR-11325
罗卡斯汀 罗卡斯汀Chemical Name: 2-[2-(Dimethylaminoethyl)-3,4-dihydro-4-methylpyrido[3,2-f]-1,4-oxazepine-5(2H)-thione (E)-2-butenedioate
CAS No. 91833-50-0, 91833-49-7 (free base), 91833-77-1 (free base, racemic)
项目整合开发状态: Phase II
项目研究机构: Wyeth Consumer Healthcare (Originator)
合成路线:The condensation of 3-hydroxy-1-methylpyrrolidine (I) with 2-chloronicotinic acid (II) by means of NaH in DMSO gives sodium 2-(1-methylpyrrolidin-3-yloxy)pyridine-3-carboxylate (III),which is then cyclized by a treatment with dry HCl in chloroform followed by a reaction with triphenylphosphine and CCl4 yielding finally 2-(2-chloroethyl)-4-methyl-3,4-dihydropyrido[3,2-f]-1,4-oxazepin-5(2H)-one (IV).The reaction of (IV) with P2S5 and K2S in refluxing toluene affords the corresponding thione (V),which is finally treated with 40% aqueous dimethylamine in ethanol at 100 C in a pressure vessel,and with fumaric acid (VI) in methanol.
📌 参考资料/链接：
参考文献标题:Fused aromatic oxazepinones and sulphur analogues thereof and their preparation and use in counteracting histamine
文献作者:Cale,A.D.Jr.; Franko,B.V.; Leonard,C.A.(A.H.Robins Co.Inc.)
参考来源:EP 0107930; ES 8607956; ES 8802574; US 4592866; US 4604388
📄 详细内容
合成路线:The condensation of 3-hydroxy-1-methylpyrrolidine (I) with 2-chloronicotinic acid (II) by means of NaH in DMSO gives sodium 2-(1-methylpyrrolidin-3-yloxy)pyridine-3-carboxylate (III),which is then cyclized by a treatment with dry HCl in chloroform followed by a reaction with triphenylphosphine and CCl4 yielding finally 2-(2-chloroethyl)-4-methyl-3,4-dihydropyrido[3,2-f]-1,4-oxazepin-5(2H)-one (IV).The reaction of (IV) with P2S5 and K2S in refluxing toluene affords the corresponding thione (V),which is finally treated with 40% aqueous dimethylamine in ethanol at 100 C in a pressure vessel,and with fumaric acid (VI) in methanol.
参考文献标题:AHR-11325
文献作者:Pento,J.T.; Castar,R.M.; Serradell,M.N.; Castar,J.
参考来源:Drugs Fut 1987,12(10),924
产品链接: CAS No.91833-49-7›› 产品链接: CAS No.91833-77-1››