Cimicoxib, UR-8880
4-[4-氯-5-(3-氟-4-甲氧基苯基)-1H-咪唑-1-基]苯磺酰胺Chemical Name: 4-[4-Chloro-5-(3-fluoro-4-methoxyphenyl)-1H-imidazol-1-yl]benzenesulfonamide
CAS No. 265114-23-6
项目整合开发状态: Phase II
项目研究机构: Uriach (Originator)
合成路线:Treatment of 4-(acetylamino)phenylsulfonyl chloride (I) with tert-butylamine yields sulfonamide (II),which on deprotection with potassium hydroxide gives amine (III).Reaction of compound (III) with 4-methoxy-3-fluorobenz-aldehyde gives imine (IV),which is cyclized with tosylmethyl isocyanide to afford imidazole (V).Regioselective chlorination of compound (V) with N-chlorosuccinimide (NCS) to afford the chloroimidazole (VI) and then deprotection of the sulfonamide group of (VI) yields cimicoxib in 40% overall yield.
📌 参考资料/链接：
参考文献标题:Novel imidazoles with anti-inflammatory activity
文献作者:Almansa,C.; Torres,M.C.; Gonzalez,C.(J.Uriach & C韆.,SA)
参考来源:EP 1122243; JP 2002527508; WO 0023426
📄 详细内容
合成路线:Treatment of 4-(acetylamino)phenylsulfonyl chloride (I) with tert-butylamine yields sulfonamide (II),which on deprotection with potassium hydroxide gives amine (III).Reaction of compound (III) with 4-methoxy-3-fluorobenz-aldehyde gives imine (IV),which is cyclized with tosylmethyl isocyanide to afford imidazole (V).Regioselective chlorination of compound (V) with N-chlorosuccinimide (NCS) to afford the chloroimidazole (VI) and then deprotection of the sulfonamide group of (VI) yields cimicoxib in 40% overall yield.
参考文献标题:Method of preparing 4-(imidazol-1-yl)benzenesulphonamide derivs.
文献作者:Almansa Rosales,C.; Gonzales Gonzales,C.(J.Uriach & C韆.,SA)
参考来源:ES 2184633; WO 0316285
合成路线:Treatment of 4-(acetylamino)phenylsulfonyl chloride (I) with tert-butylamine yields sulfonamide (II),which on deprotection with potassium hydroxide gives amine (III).Reaction of compound (III) with 4-methoxy-3-fluorobenz-aldehyde gives imine (IV),which is cyclized with tosylmethyl isocyanide to afford imidazole (V).Regioselective chlorination of compound (V) with N-chlorosuccinimide (NCS) to afford the chloroimidazole (VI) and then deprotection of the sulfonamide group of (VI) yields cimicoxib in 40% overall yield.
参考文献标题:Cimicoxib
文献作者:Sorbera,L.A.; Ramis,I.
参考来源:Drugs Fut 2004,29(4),325
产品链接: CAS No. 265114-23-6››