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项目整合精选>>>Pariprazole sodium, Rabeprazole sodium, LY-307640, E-3810, Aciphex, Pariet
Pariprazole sodium, Rabeprazole sodium, LY-307640, E-3810, Aciphex, Pariet
雷贝拉唑钠 雷贝拉唑 Chemical Name: 2-[4-(3-Methoxypropoxy)-3-methylpyridin-2-ylmethylsulfinyl]benzimidazole 1-sodium salt
CAS No. 117976-90-6, 117976-89-3 (free acid)
项目整合开发状态: Launched-1997
项目研究机构: Eisai (Originator), Janssen (Licensee), Janssen-Cilag (Licensee)
合成路线:The condensation of 4-chloro-2,3-dimethylpyridine N-oxide (I) with 3-methoxypropanol (II) by means of NaH in DMSO gives 4-(3-methoxypropoxy)-2,3-dimethylpyridine N-oxide (III),which is treated with acetic anhydride at 90 C yielding 2-(acetoxymethyl)-4-(3-methoxypropoxy)-3-methylpyridine (IV).The hydrolysis of (IV) with NaOH in ethanol affords 2-(hydroxymethyl)-4-(3-methoxypropoxy)-3-methylpyridine (V),which by treatment with SOCl2 in dichloromethane is converted into 2-(chloromethyl)-4-(3-methoxypropoxy)-3-methylpyridine (VI).The condensation of (VI) with 2-mercaptobenzimidazole (VII) by means of NaOH in ethanol gives 2-[4-(3-methoxypropoxy)-3-methylpyridin-2-ylmethylthio]benzimidazole (VIII),which is oxidized with m-chloroperbenzoic acid in ether - dichloromethane to afford 2-[4-(3-methoxypropoxy)-3-methylpyridin-2-ylsulfinyl]benzimidazole (IX).Finally,this compound is treated wtih aqueous Na2CO3.
📌 参考资料/链接：
参考文献标题:Pyridine derivs.,pharmaceutical compsns.comprising the same,the use of the same for the manufacture of medicaments having therapeutic or preventative value,and a process for preparing the same
文献作者:Souda,S.; Ueda,N.; Miyazawa,S.; Tagami,K.; Nomoto,S.; Okita,M.; Shimomura,N.; Kaneko,T.; Fujimoto,M.; Murakami,M.; Oketani,K.; Fujisaki,H.; Shibata,H.; Wakabayashi,T.(Eisai Co.,Ltd.)
参考来源:AU 8781138; EP 0268956; EP 0475456; EP 0654471; EP 0786461; JP 1989006270; JP 1993247035; JP 1995291967; US 5045552; US 5998445
📄 详细内容
合成路线:The condensation of 4-chloro-2,3-dimethylpyridine N-oxide (I) with 3-methoxypropanol (II) by means of NaH in DMSO gives 4-(3-methoxypropoxy)-2,3-dimethylpyridine N-oxide (III),which is treated with acetic anhydride at 90 C yielding 2-(acetoxymethyl)-4-(3-methoxypropoxy)-3-methylpyridine (IV).The hydrolysis of (IV) with NaOH in ethanol affords 2-(hydroxymethyl)-4-(3-methoxypropoxy)-3-methylpyridine (V),which by treatment with SOCl2 in dichloromethane is converted into 2-(chloromethyl)-4-(3-methoxypropoxy)-3-methylpyridine (VI).The condensation of (VI) with 2-mercaptobenzimidazole (VII) by means of NaOH in ethanol gives 2-[4-(3-methoxypropoxy)-3-methylpyridin-2-ylmethylthio]benzimidazole (VIII),which is oxidized with m-chloroperbenzoic acid in ether - dichloromethane to afford 2-[4-(3-methoxypropoxy)-3-methylpyridin-2-ylsulfinyl]benzimidazole (IX).Finally,this compound is treated wtih aqueous Na2CO3.
参考文献标题:E-3810
文献作者:Castar,J.; Prous,J.
参考来源:Drugs Fut 1991,16(1),19
合成路线:A synthesis for [14C]-labeled E-3810 has been described:The cyclization of o-phenylenediamine (I) with [14C]-labeled carbon disulfide (II) by means of aqueous KOH gives the potassium salt of [14C]-2-mercaptobenzimidazole (III),which is treated with acetic acid to obtain the corresponding thiol (IV).The condensation of (IV) with 2-(chloromethyl)-4-(3-methoxypropoxy)-3-methylpyridine (V) by means of NaOH in refluxing ethanol yields [14C]-labeled 2-[4-(3-methoxypropoxy)-3-methylpyridin-3-ylmethylthio]benzimidazole (VI).The oxidation of (VI) with m-chloroperbenzoic acid in dichloromethane affords the corresponding sulfoxide (VIII),which is finally treated with 0.1 N NaOH in ethanol.
参考文献标题:Synthesis of 14C-labelled sodium pariprazole (E3810)
文献作者:Sohda,S.; Tagami,K.; Chiku,S.
参考来源:J Label Compd Radiopharm 1993,33(9),849
产品链接: CAS No. 117976-90-6›› 产品链接: CAS No.117976-89-3››