新产品编号:1933713
Chemical Name: 1-(4-Benzyl-2-cyclohexyloxazol-5-ylmethyl)-4-(2-methoxyphenyl)piperazine
项目整合开发状态: Biological Testing
项目研究机构: Wyeth Pharmaceuticals (Originator)
合成路线:By condensation of azacycloheptan-2-one (I) with 1-bromododecane (II) by means of NaH in refluxing toluene.
合成路线:Coupling of piperazine (I) with chloro derivative (II) by means of K2CO3 and KI in acetone affords protected compound (III),which is then condensed with acid chloride (IV) by means of n-BuLi in THF to yield amide (V).Deprotection of (V) by hydrogenation over Pd/C in EtOH provides (VI),which is finally cyclized by treatment with POCl3 in DMF.Alternatively,the synthesis of the target product can be achieved by an analogous route: Acylation of amine (VII) with acid chloride (IV) by means of K2CO3 in CH2Cl2 provides amide (VIII),which is then cyclized by heating with POCl3 in DMF/benzene to give oxazole (IX).Finally,(IX) is condensed with piperazine (I) by means of K2CO3 and KI in acetone.
📌 参考资料/链接：
参考文献标题:Trisubstd.oxazole derivs.as serotonin ligands
文献作者:Kelly,M.G.; Greenblatt,L.P.; Nelson,F.C.(American Home Products Corp.)
参考来源:US 6242448
📄 详细内容
合成路线:Coupling of piperazine (I) with chloro derivative (II) by means of K2CO3 and KI in acetone affords protected compound (III),which is then condensed with acid chloride (IV) by means of n-BuLi in THF to yield amide (V).Deprotection of (V) by hydrogenation over Pd/C in EtOH provides (VI),which is finally cyclized by treatment with POCl3 in DMF.Alternatively,the synthesis of the target product can be achieved by an analogous route: Acylation of amine (VII) with acid chloride (IV) by means of K2CO3 in CH2Cl2 provides amide (VIII),which is then cyclized by heating with POCl3 in DMF/benzene to give oxazole (IX).Finally,(IX) is condensed with piperazine (I) by means of K2CO3 and KI in acetone.
参考文献标题:Novel trisubstituted oxazole derivatives as 5-HT1A receptor ligands
文献作者:Schechter,L.E.; Smith,D.L.; Nelson,F.C.; Greenblatt,L.P.; Kelly,M.G.
参考来源:220th ACS Natl Meet (Aug 20 2000,Washington DC) 2000,Abst MEDI 117