Proxodolol
(±)-1-(叔丁胺)-3-[2-(3-甲基-1,2,4-噁二唑-5-甲氧基)苯氧基]-2-盐酸丙醇 2-丙醇,1-[(1,1-二甲基乙基)氨基]-[2-[(3-甲氧基-1,2,4-噁二唑-5-基)甲氧基]-,盐酸盐(1:1) 1-(叔丁基乙氨基)-3-{2-[(3-甲基-1,2,4-噁二唑-5-基)甲氧基]苯氧基}丙烷-2-醇Chemical Name: (?-1-(tert-Butylamino)-3-[2-(3-methyl-1,2,4-oxadiazol-5-ylmethoxy)phenoxy]-2-propanol hydrochloride; (?-5-[2-(3-tert-Butylamino-2-hydroxypropoxy)phenoxymethyl]-3-methyl-1,2,4-oxadiazole hydrochloride
CAS No. 152289-59-3, 158446-41-4 (error), 152289-58-2 (free base)
项目整合开发状态: Phase II
项目研究机构: Center for Chemistry of Drugs (Originator)
合成路线:Proxodolol (V) was obtained as shown in Scheme 21696501a:Monoalkylation of pyrocatechol with chloroacetic acid gives 2-hydroxyphenoxyacetic acid (I),which is cyclized on heating into 1,4-benzodioxan-2-one (II).Condensation of (II) with acetamidoxime,giving 2-methyl-5-(2-hydroxyphenoxymethyl)-1,2,4-oxadiazole (III),followed by alkylation with epichlorohydrin yields the corresponding diether (IV),which smoothly reacts with tert-BuNH2,and the amine (V) is converted into its hydrochloride by reaction with HCl.
📌 参考资料/链接：
参考文献标题:The hydrochlorides of derivs.of 5-phenoxymethyl-1,2,4-oxadiaxole,possessing beta- and alpha-adrenoblocking activities
文献作者:Sokolov,S.D.; Vinogradova,S.M.; Azarevich,O.G.; Berg,M.V.; Mashkovski,M.D.; Yuzhakov,S.D.; Morozov,A.V.(Center for Chemistry of Drugs)
参考来源:SU 1132505
📄 详细内容
合成路线:Proxodolol (V) was obtained as shown in Scheme 21696501a:Monoalkylation of pyrocatechol with chloroacetic acid gives 2-hydroxyphenoxyacetic acid (I),which is cyclized on heating into 1,4-benzodioxan-2-one (II).Condensation of (II) with acetamidoxime,giving 2-methyl-5-(2-hydroxyphenoxymethyl)-1,2,4-oxadiazole (III),followed by alkylation with epichlorohydrin yields the corresponding diether (IV),which smoothly reacts with tert-BuNH2,and the amine (V) is converted into its hydrochloride by reaction with HCl.
参考文献标题:The method for producing of 5-(2-hydroxyphenoxymethyl)-1,2,4-oxadiazoles
文献作者:Sokolov,S.D.; Vinogradova,S.M.; Azarevich,O.G.(Center for Chemistry of Drugs)
参考来源:SU 1139129
合成路线:Proxodolol (V) was obtained as shown in Scheme 21696501a:Monoalkylation of pyrocatechol with chloroacetic acid gives 2-hydroxyphenoxyacetic acid (I),which is cyclized on heating into 1,4-benzodioxan-2-one (II).Condensation of (II) with acetamidoxime,giving 2-methyl-5-(2-hydroxyphenoxymethyl)-1,2,4-oxadiazole (III),followed by alkylation with epichlorohydrin yields the corresponding diether (IV),which smoothly reacts with tert-BuNH2,and the amine (V) is converted into its hydrochloride by reaction with HCl.
参考文献标题:Proxodolol
文献作者:Mashkovski,M.D.; Sokolov,S.D.; Vinogradova,S.M.; Yuzhakov,S.D.; Yermakova,V.N.
参考来源:Drugs Fut 1997,22(5),499