T-82
Chemical Name: 2-[2-(1-Benzylpiperidin-4-yl)ethyl]-9-methoxy-2,3-dihydro-1H-pyrrolo[3,4-b]quinolin-1-one hemifumarate
CAS No. 142471-56-5 (free base)
项目整合开发状态: Phase II
项目研究机构: SSP (Originator), Arena (Licensee)
合成路线:The reaction of methyl anthranilate (I) with tetrahydrofuran-2,4-dione (II) by means of HCl in ethanol gives 2-(5-oxo-2,5-dihydrofuran-3-ylamino)benzoic acid methyl ester (III),which is cyclized by means of polyphosphoric acid (PPA) at 130-140 C yielding the tricyclic hydroxyketone (IV).The condensation of (IV) with 4-(2-aminoethyl)-1-benzylpiperidine (V) in N-methyl-2-pyrrolidone by a Dean-Stark elimination of water affords 2-[2-(1-benzyl-piperidin-4-yl)ethyl]-9-hydroxy-2,3-dihydro-1H-pyrrolo[3,4-b]quinolin-1-one (VI),which is finally methylated with diazomethane in methanol.
📌 参考资料/链接：
参考文献标题:Quinoline derivs.
文献作者:Hasegawa,H.; Isomae,K.; Kotsugai,T.; Shioiri,N.; Sekine,K.; Taido,N.; Sato,S.; Kuraishi,T.(SSP Co.,Ltd.)
参考来源:EP 0481429; JP 1993009188; JP 1993279355; US 5190951; US 5240934; US 5300517
📄 详细内容
合成路线:The reaction of methyl anthranilate (I) with tetrahydrofuran-2,4-dione (II) by means of HCl in ethanol gives 2-(5-oxo-2,5-dihydrofuran-3-ylamino)benzoic acid methyl ester (III),which is cyclized by means of polyphosphoric acid (PPA) at 130-140 C yielding the tricyclic hydroxyketone (IV).The condensation of (IV) with 4-(2-aminoethyl)-1-benzylpiperidine (V) in N-methyl-2-pyrrolidone by a Dean-Stark elimination of water affords 2-[2-(1-benzyl-piperidin-4-yl)ethyl]-9-hydroxy-2,3-dihydro-1H-pyrrolo[3,4-b]quinolin-1-one (VI),which is finally methylated with diazomethane in methanol.
参考文献标题:T-82
文献作者:Castar,J.; Mucke,H.A.M.
参考来源:Drugs Fut 1998,23(10),1075-1077
产品链接: CAS No. 142471-56-5››