XU-817
Chemical Name: 1-[2-(4-Benzylpiperidin-1-yl)-2-oxoethyl]-1H-indole-5-carboxamidine
CAS No. 202123-75-9
项目整合开发状态: Preclinical
项目研究机构: Bristol-Myers Squibb (Originator)
合成路线:The alkylation of 5-cyanoindole (I) with methyl bromoacetate (II) in the presence of NaH in DMF provided the indolylacetate ester (III),which was hydrolyzed to the corresponding carboxylic acid (IV) with methanolic KOH.Coupling of (IV) with 4-benzylpiperidine (V) employing 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide-HCl (EDC) afforded amide (VI).Pinner reaction of (VI) with methanolic HCl produced imidate (VII),which was finally treated with ammonium carbonate in MeOH to yield the target amidine
📌 参考资料/链接：
参考文献标题:Amidinoindoles,amidinoazoles,and analogs thereof as inhibitors of factor Xa and of thrombin
文献作者:Dominguez,C.; Han,Q.; Duffy,D.E.; Park,J.M.; Quan,M.L.; Rossi,K.A.; Wexler,R.R.(DuPont Pharmaceuticals Co.)
参考来源:EP 0960102; WO 9801428
📄 详细内容
合成路线:The alkylation of 5-cyanoindole (I) with methyl bromoacetate (II) in the presence of NaH in DMF provided the indolylacetate ester (III),which was hydrolyzed to the corresponding carboxylic acid (IV) with methanolic KOH.Coupling of (IV) with 4-benzylpiperidine (V) employing 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide-HCl (EDC) afforded amide (VI).Pinner reaction of (VI) with methanolic HCl produced imidate (VII),which was finally treated with ammonium carbonate in MeOH to yield the target amidine
参考文献标题:Design and synthesis of potent and selective 5,6-fused heterocyclic thrombin inhibitors
文献作者:Dominguez,C.; Duffy,D.E.; Han,Q.; Alexander,R.S.; Galemmo,R.A.Jr.; Park,J.M.; Wong,P.C.; Amparo,E.C.; Knabb,R.M.; Luettgen,J.; Wexler,R.R.
参考来源:Bioorg Med Chem Lett 1999,9(7),925