Zinviroxime((Z)-isomer), Enviroxime, AR-336, LY-122772
恩韦肟 韦罗肟 恩韦肟Chemical Name: (E)-2-Amino-6-benzoyl-1-(isopropylsulfonyl)benzimidazole oxime
CAS No. 72301-79-2, 72301-78-1 ((Z)-isomer), 63198-97-0 (undefined stereoch.)
项目整合开发状态: Phase II
项目研究机构: Lilly (Originator)
合成路线:The acetylation of 4-aminobenzophenone (I) with acetic anhydride in hot benzene gives 4-acetamidobenzophenone (II),which is nitrated with 90% HNO3 in acetic acid-acetic anhydride yielding 4-acetamido-3-nitrobenzophenone (III).The hydrolysis of (III) with H2SO4 affords 4-amino-3-nitrobenzophenone (IV),which is reduced with H2 over Raney-Ni in THF to give 3,4-diaminobenzophenone (V).The cyclization of (V) with cyanogen bromide in methanol-water gives rise to 2-amino-5-benzoylbenzimidazol (VI),which is treated with isopropylsulfonyl chloride (A) and NaH in dimethoxyethane affording 2-amino-1-isopropylsulfonyl-6-benzoylbenzimidazol (VII).Finally,this compound is treated with hydroxylamine hydrochloride in refluxing methanol.
📌 参考资料/链接：
参考文献标题:AR-336
文献作者:Castar,J.; Hopkins,S.J.
参考来源:Drugs Fut 1980,5(3),120
📄 详细内容
合成路线:The acetylation of 4-aminobenzophenone (I) with acetic anhydride in hot benzene gives 4-acetamidobenzophenone (II),which is nitrated with 90% HNO3 in acetic acid-acetic anhydride yielding 4-acetamido-3-nitrobenzophenone (III).The hydrolysis of (III) with H2SO4 affords 4-amino-3-nitrobenzophenone (IV),which is reduced with H2 over Raney-Ni in THF to give 3,4-diaminobenzophenone (V).The cyclization of (V) with cyanogen bromide in methanol-water gives rise to 2-amino-5-benzoylbenzimidazol (VI),which is treated with isopropylsulfonyl chloride (A) and NaH in dimethoxyethane affording 2-amino-1-isopropylsulfonyl-6-benzoylbenzimidazol (VII).Finally,this compound is treated with hydroxylamine hydrochloride in refluxing methanol.
参考文献标题:
文献作者:Paget,C.J.; et al.
参考来源:DE 2638551