Clofurenadine hydrochloride, (?-BN-1267
Chemical Name: (?-3-(4-Chlorophenyl)-1,3-dihydro-3,6-dimethylfuro[3,4-c]pyridin-7-ol hydrochloride
CAS No. 91868-84-7 (free base)
项目整合开发状态: Phase I
项目研究机构: Institut Henri Beaufour (Originator)
合成路线:The synthesis of (rac)-BN-1267 is presented.The Grignard reaction of 2,2,8-trimethyl-5-formylpyrido[4,3-e]-1,3-dioxane (I) with 4-chloro phenyl magnesium bromide in refluxing ether gives 2,2,8-trimethyl-5-(4-chloro-alpha-hydroxybenzyl)pyrido[4,3-e]-1,3-dioxane (II),which by oxidation with MnO2 affords the corresponding ketone (III).The Grignard reaction of (III) with methyl maynesium iodide gives 2,2,8-trimethyl-5-(4-chloro-alpha-methyl-alpha-hydraxybenzyl)pyrido[4,3-e]-1,3-dioxane (IV),which is then hydrolyzed and cyclized by treatment with aqueous concentrated HCl.
📌 参考资料/链接：
参考文献标题:Furo[3,4-c]pyridine derivatives and therapeutic compositions containing the same
文献作者:Esanu,A.(SCRAS (Societ?de Conseils de Recherches et d'Applications Scientifiques))
参考来源:BE 0899222; CH 660191; GB 2137618; JP 1984193888; US 4581363; US 4735950
📄 详细内容
合成路线:The synthesis of (rac)-BN-1267 is presented.The Grignard reaction of 2,2,8-trimethyl-5-formylpyrido[4,3-e]-1,3-dioxane (I) with 4-chloro phenyl magnesium bromide in refluxing ether gives 2,2,8-trimethyl-5-(4-chloro-alpha-hydroxybenzyl)pyrido[4,3-e]-1,3-dioxane (II),which by oxidation with MnO2 affords the corresponding ketone (III).The Grignard reaction of (III) with methyl maynesium iodide gives 2,2,8-trimethyl-5-(4-chloro-alpha-methyl-alpha-hydraxybenzyl)pyrido[4,3-e]-1,3-dioxane (IV),which is then hydrolyzed and cyclized by treatment with aqueous concentrated HCl.
参考文献标题:Clofurenadine hydrochloride
文献作者:Esanu,A.; Etienne,A.; Laurent,J.-P.; Braquet,P.; Mencia Huerta,J.M.Clostre,F.; Touvay,C.
参考来源:Drugs Fut 1987,12(7),627
合成路线:The synthesis of (rac)-BN-1267 is presented.The Grignard reaction of 2,2,8-trimethyl-5-formylpyrido[4,3-e]-1,3-dioxane (I) with 4-chloro phenyl magnesium bromide in refluxing ether gives 2,2,8-trimethyl-5-(4-chloro-alpha-hydroxybenzyl)pyrido[4,3-e]-1,3-dioxane (II),which by oxidation with MnO2 affords the corresponding ketone (III).The Grignard reaction of (III) with methyl maynesium iodide gives 2,2,8-trimethyl-5-(4-chloro-alpha-methyl-alpha-hydraxybenzyl)pyrido[4,3-e]-1,3-dioxane (IV),which is then hydrolyzed and cyclized by treatment with aqueous concentrated HCl.
参考文献标题:
文献作者:De Salvia,R.; et al.
参考来源:J Meet Franco-Ital Pharmacol Soc (June,Paris) 1984,135(1-2),1