Emapunil, SX-5216, AC-5216
依马普尼Chemical Name: N-Benzyl-N-ethyl-2-(7-methyl-8-oxo-2-phenyl-7,8-dihydro-9H-purin-9-yl)acetamide
CAS No. 226954-04-7
项目整合开发状态: Phase I
项目研究机构: Dainippon Pharmaceutical (Originator), Novartis (Licensee)
合成路线:Pyrimidinone (III) was formed by condensation of benzamidine hydrochloride (I) with diethyl (ethoxymethylene)malonate (II).Subsequent reaction with glycinamide derivative (V) in the presence of p-tosyl chloride and Et3N afforded the aminopyrimidine (VI) (1).Alternatively,aminopyrimidine (VI) was prepared by chlorination of pyrimidinone (III) with POCl3,followed by displacement of the resulting chloropyrimidine (IV) with glycinamide (V) (2).Basic hydrolysis of the ethyl ester group of (VI) furnished pyrimidinecarboxylic acid (VII).This was then subjected to a Curtius rearrangement employing diphenyl phosphoryl azide (DPPA) to produce the 8-oxopurine system (VIII).Finally,N-alkylation of (VIII) with iodomethane gave rise to the title compound.
📌 参考资料/链接：
参考文献标题:2-Aryl-8-oxodihydropurine derivs.,process for producing the same,medicinal compsns.containing the same,and intermediates thereof
文献作者:Matsumoto,K.; Kondo,K.; Furukawa,K.; Murata,T.; Oka,M.(Dainippon Pharmaceutical Co.,Ltd.)
参考来源:EP 1036794; WO 9928320
📄 详细内容
合成路线:Pyrimidinone (III) was formed by condensation of benzamidine hydrochloride (I) with diethyl (ethoxymethylene)malonate (II).Subsequent reaction with glycinamide derivative (V) in the presence of p-tosyl chloride and Et3N afforded the aminopyrimidine (VI) (1).Alternatively,aminopyrimidine (VI) was prepared by chlorination of pyrimidinone (III) with POCl3,followed by displacement of the resulting chloropyrimidine (IV) with glycinamide (V) (2).Basic hydrolysis of the ethyl ester group of (VI) furnished pyrimidinecarboxylic acid (VII).This was then subjected to a Curtius rearrangement employing diphenyl phosphoryl azide (DPPA) to produce the 8-oxopurine system (VIII).Finally,N-alkylation of (VIII) with iodomethane gave rise to the title compound.
参考文献标题:SX-5216,highly potent and selective mitochondrial benzodiazepine receptor ligand as a potential anxiolytic agent
文献作者:Masumoto,K.; et al.
参考来源:219th ACS Natl Meet (March 26 2000,San Francisco) 2000,Abst MEDI 113
产品链接: CAS No. 226954-04-7››