SB-265610

1-(2-溴苯基)-3-(4-氰基-1H-苯并三唑-7-基)脲Chemical Name: N-(2-Bromophenyl)-N'-(4-cyano-1H-1,2,3-benzotriazol-7-yl)urea
CAS No. 211096-49-0
项目整合开发状态: Preclinical
项目研究机构: GlaxoSmithKline (Originator)
合成路线:Reaction of 2-bromo-5-nitroaniline (I) with cuprous cyanide in the presence of pyridine in hot DMF afforded the 2-aminobenzonitrile (II).This was converted to the phenylenediamine derivative (III) upon treatment with tetramethylhydrazine iodide in the presence of sodium tert-pentoxide.The target benzotriazole system (IV) was then produced by diazotization of diamine (III) with NaNO2 in hot HOAc.Subsequent nitro group reduction by catalytic hydrogenation yielded 7-amino-4-cyanobenzotriazole (V).The aminobenzotriazole (V) was finally converted to the desired urea by condensation with 2-bromophenyl isocyanate (VI) in hot DMF.
📌 参考资料/链接:
参考文献标题:IL-8 receptor antagonists
文献作者:Widdowson,K.L.; Rutledge,M.C.(GlaxoSmithKline Inc.)
参考来源:EP 0991406; JP 2001511130; US 6300325; WO 9832439

📄 详细内容


合成路线:Reaction of 2-bromo-5-nitroaniline (I) with cuprous cyanide in the presence of pyridine in hot DMF afforded the 2-aminobenzonitrile (II).This was converted to the phenylenediamine derivative (III) upon treatment with tetramethylhydrazine iodide in the presence of sodium tert-pentoxide.The target benzotriazole system (IV) was then produced by diazotization of diamine (III) with NaNO2 in hot HOAc.Subsequent nitro group reduction by catalytic hydrogenation yielded 7-amino-4-cyanobenzotriazole (V).The aminobenzotriazole (V) was finally converted to the desired urea by condensation with 2-bromophenyl isocyanate (VI) in hot DMF.
参考文献标题:IL-8 receptor antagonists
文献作者:Widdowson,K.L.; Rutledge,M.C.; Benson,G.M.(GlaxoSmithKline Inc.)
参考来源:WO 0076501


产品链接: CAS No. 211096-49-0››