新产品编号:283687
Chemical Name: 5-(4-Aminophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepin-8-one
CAS No. 197368-49-3
项目整合开发状态: Preclinical
项目研究机构: Acea (Originator)
合成路线:Esterification of 3,4-(methylenedioxy)phenylacetic acid (I) with methanol in the presence of sulfuric acid provided methyl ester (II).Fiedel Crafts acylation of (II) with 4-nitrobenzoic acid (III) under the action of P2O5 in refluxing dichloroethane yielded ketone (IV).This compound was refluxed with hydrazine hydrate in ethanol to afford benzodiazepinone (V).Finally,the nitro group was reduced by hydrogenation in acetic acid with Pd/C as the catalyst or with Raney-Ni and hydrazine to give the corresponding amine.
📌 参考资料/链接：
参考文献标题:Substd.2,3-benzodiazepin-4-ones and the use thereof
文献作者:Xia,H.; Field,G.; Lan,N.C.; Wang,Y.(Acea Pharmaceuticals)
参考来源:EP 1021418; JP 2000506890; US 5891871; WO 9734878
📄 详细内容
合成路线:Esterification of 3,4-(methylenedioxy)phenylacetic acid (I) with methanol in the presence of sulfuric acid provided methyl ester (II).Fiedel Crafts acylation of (II) with 4-nitrobenzoic acid (III) under the action of P2O5 in refluxing dichloroethane yielded ketone (IV).This compound was refluxed with hydrazine hydrate in ethanol to afford benzodiazepinone (V).Finally,the nitro group was reduced by hydrogenation in acetic acid with Pd/C as the catalyst or with Raney-Ni and hydrazine to give the corresponding amine.
参考文献标题:Synthesis of 7,8-(methylenedioxy)-1-phenyl-3,5-dihydro-4H-2,3-benzodiazepin-4-ones as novel and potent noncompetitive AMPA receptor antagonists
文献作者:Wang,Y.; Konkoy,C.S.; Ilyin,V.I.; Vanover,K.E.; Carter,R.B.; Weber,E.; Keana,J.F.; Woodward,R.M.; Cai,S.X.
参考来源:J Med Chem 1998,41(14),2621