FK-3311
N-[4-乙酰基-2-(2,4-二氟苯氧基)苯基]-甲烷磺酰胺Chemical Name: 4-Acetyl-2-(2,4-difluorophenoxy)methanesulfonanilide; 3-(2,4-Difluorophenoxy)-4-(methanesulfonamido)acetophenone; N-[4-Acetyl-2-(2,4-difluorophenoxy)phenyl]methanesulfonamide
CAS No. 116686-15-8
项目整合开发状态: Phase II
项目研究机构: Fujisawa (Originator)
合成路线:This compound has been obtained by two different ways:1) The oxidation of 4'-amino-3'-chloroacetophenone (I) with NaNO2 and HCl in water gives 3'-chloro-4-nitroacetophenone (II),which is condensed with 2,4-difluorophenol (III) by means of K2CO3 in xylene yielding 3'-(2,4-difluorophenyl)-4'-nitroacetophenone (IV).The reduction of (IV) with Fe and NH4Cl in ethanol affords the corresponding 4'-amino compound (V),which is finally treated with methanesulfonyl chloride and pyridine.2) The reaction of 4'-aminoacetophenone (VI) with methanesulfonyl chloride as before gives the corresponding sulfonamide (VII),which is brominated with Br2 in acetic acid yielding N-(4-acetyl-3-bromophenyl)methanesulfonamide (VIII).Finally,this compound is condensed with 2,4-difluorophenol (III) by means of K2CO3 and CuCl as before.
📌 参考资料/链接：
参考文献标题:Studies on antiinflammatory agents.I.Synthesis and pharmacological properties of 2'-phenoxymethanesulfonanilide derivatives
文献作者:Tsuji,K.; Nakamura,K.; Konishi,N.; Okumura,H.; Matsuo,M.
参考来源:Chem Pharm Bull 1992,40(9),2399
📄 详细内容
合成路线:This compound has been obtained by two different ways:1) The oxidation of 4'-amino-3'-chloroacetophenone (I) with NaNO2 and HCl in water gives 3'-chloro-4-nitroacetophenone (II),which is condensed with 2,4-difluorophenol (III) by means of K2CO3 in xylene yielding 3'-(2,4-difluorophenyl)-4'-nitroacetophenone (IV).The reduction of (IV) with Fe and NH4Cl in ethanol affords the corresponding 4'-amino compound (V),which is finally treated with methanesulfonyl chloride and pyridine.2) The reaction of 4'-aminoacetophenone (VI) with methanesulfonyl chloride as before gives the corresponding sulfonamide (VII),which is brominated with Br2 in acetic acid yielding N-(4-acetyl-3-bromophenyl)methanesulfonamide (VIII).Finally,this compound is condensed with 2,4-difluorophenol (III) by means of K2CO3 and CuCl as before.
参考文献标题:Process development of a novel anti-inflammatory agent.The regiospecific bromination of 4'-acetylmethanesulfonanilide
文献作者:Zanka,A.; et al.
参考来源:Org Process Res Dev 1998,2(2),71
产品链接: CAS No. 116686-15-8››