Renzapride hydrochloride, ATL-1251, AZM-112, BRL-24924
伦扎必利 4-氨基-N-[(1S,4R,5S)-1-氮杂双环[3.3.1]壬烷-4-基]-5-氯-2-甲氧基-苯甲酰胺 Chemical Name: (?-endo-4-Amino-5-chloro-2-methoxy-N-(1-azabicyclo[3.3.1]non-4-yl)benzamide hydrochloride
CAS No. 112727-80-7 (free base), 88721-77-1 (free base, no stereoch.)
项目整合开发状态: Phase II
项目研究机构: GlaxoSmithKline (Originator), Alizyme (Licensee)
合成路线:The reaction of 1-azabicyclo[3.3.1]nonan-4-one (I) with hydroxyamine gives the corresponding oxime (II),which is reduced with LiAlH4 in THF yielding 4-amino-1-azabicyclo [3.3.1]nonane (III).Finally,this compound is condensed with 4-amino-5-chloro-2-methoxybenzoylchloride (IV).
📌 参考资料/链接：
参考文献标题:Azabicyclo compounds,useful as intermediates
文献作者:King,F.D.(SmithKline Beecham plc)
参考来源:EP 0094742; JP 5194513; JP 58188885; US 4857647
📄 详细内容
合成路线:The reaction of 1-azabicyclo[3.3.1]nonan-4-one (I) with hydroxyamine gives the corresponding oxime (II),which is reduced with LiAlH4 in THF yielding 4-amino-1-azabicyclo [3.3.1]nonane (III).Finally,this compound is condensed with 4-amino-5-chloro-2-methoxybenzoylchloride (IV).
参考文献标题:BRL-24924
文献作者:Serradell,M.N.; Castar,R.M.; Castar,J.
参考来源:Drugs Fut 1987,12(11),1009
合成路线:A new synthesis of renzapride has been described:The reaction of 1-azabicyclo[3.3.1]nonan-4-one (I) with hydroxylamine and pyridine in refluxing ethanol gives the corresponding oxime (II),which is reduced with Na in refluxing pentanol yielding a mixture of the exo- and endo-amines (IIIa and IIIb).The acylation of this mixture with 4-acetamido-5-chloro-2-methoxybenzoylchloride (IV) and triethylamine in toluene affords a mixture of the exo- and endo-amides (Va and Vb),which are separated by column chromatography over alumina.The endo-isomer (Va) is finally deacetylated with NaOH in refluxing ethanol.It is obtained as crystals,m.p.> 260 C.
参考文献标题:Substituted benzamides with conformationally restricted side chains.5.Azabicyclo[x.y.z]derivatives as 5-HT4 receptor agonists and gastric motility stimulants
文献作者:King,F.D.; Hadley,M.S.; Joiner,K.T.; Martin,R.T.; Sanger,G.J.; Smith,D.M.; Smith,G.E.; Smith,P.; Turner,D.H.; Watts,E.A.
参考来源:J Med Chem 1993,36(6),683
产品链接: CAS No. 112727-80-7›› 产品链接: CAS No.88721-77-1››