OC144-093, ONT-093, OC-144-093
(E)-4,4'-(2-(4-(3-乙氧基丙-1-烯-1-基)苯基)-1H-吡唑-4,5-二基)双(N-异丙苯胺)Chemical Name: N-[4-[2-[4-[3-Ethoxy-1(E)-propenyl]phenyl]-4-[4-(isopropylamino)phenyl]-1H-imidazol-5-yl]phenyl]-N-isopropylamine; 2-[4-[3-Ethoxy-1(E)-propenyl]phenyl]-4,5-bis[4-(isopropylamino)phenyl]-1H-imidazole
CAS No. 216227-54-2
项目整合开发状态: Phase I
项目研究机构: Ontogen (Originator)
合成路线:Palladium-catalyzed coupling of 4-bromobenzaldehyde (I) with methyl acrylate (II) furnished methyl 4-formylcinnamate (III).After aldehyde protection as the ethylene acetal (IV),ester group reduction using DIBAL in cold CH2Cl2 gave rise to the cinnamyl alcohol (V).O-Alkylation of (V) with ethyl iodide in the presence of NaH produced the corresponding ethyl ether (VI).The acetal protecting group of (VI) was then hydrolyzed with HCl to yield aldehyde (VII).
合成路线:Treatment of 4,4'-difluorobenzyl (VIII) with isopropylamine and K2CO3 in hot DMSO produced 4,4'-bis(isopropylamino)benzyl (IX).This was then condensed with the intermediate aldehyde (VII) in the presence of ammonium acetate in HOAc to produce the target triaryl imidazole.
📌 参考资料/链接：
参考文献标题:Imidazole derivs.as MDR modulators
文献作者:Zhang,C.; Mjalli,A.M.M.(Ontogen Corp.)
参考来源:EP 0999835; US 5840721; WO 9902155
📄 详细内容
合成路线:Palladium-catalyzed coupling of 4-bromobenzaldehyde (I) with methyl acrylate (II) furnished methyl 4-formylcinnamate (III).After aldehyde protection as the ethylene acetal (IV),ester group reduction using DIBAL in cold CH2Cl2 gave rise to the cinnamyl alcohol (V).O-Alkylation of (V) with ethyl iodide in the presence of NaH produced the corresponding ethyl ether (VI).The acetal protecting group of (VI) was then hydrolyzed with HCl to yield aldehyde (VII).
合成路线:Treatment of 4,4'-difluorobenzyl (VIII) with isopropylamine and K2CO3 in hot DMSO produced 4,4'-bis(isopropylamino)benzyl (IX).This was then condensed with the intermediate aldehyde (VII) in the presence of ammonium acetate in HOAc to produce the target triaryl imidazole.
参考文献标题:2,4,5-Trisubstituted imidazoles: Novel nontoxic modulators of P-glycoprotein mediated multidrug resistance.Part 2
文献作者:Zhang,C.; Sarshar,S.; Moran,E.J.; Krane,S.; Rodarte,J.C.; Benbatoul,K.D.; Dixon,R.; Mjalli,A.M.M.
参考来源:Bioorg Med Chem Lett 2000,10(23),2603
产品链接: CAS No. 216227-54-2››