新产品编号:952873
Chemical Name: 1(R)-[4-[3(R),5(S)-Dimethyl-4-(4-methyl-1,3,5-triazin-2-yl)piperazin-1-yl]-1,3,5-triazin-2-yl]ethanol
CAS No. 465530-70-5
项目整合开发状态: Preclinical
项目研究机构: Pfizer (Originator)
合成路线:Acylation of cis-2,6-dimethylpiperazine (I) with dimethylcarbamoyl chloride affords urea (II) (1,2).(R)-2-Methoxypropionamidine (III) is reacted with cyanogen bromide to produce the N-cyano amidine (IV) (1).Treatment of the carbamoyl piperazine (II) with POCl3,followed by condensation with cyanoamidine (IV) in refluxing acetonitrile gives rise to the piperazinyl triazine (V),which is condensed with 2,4-dichloro-6-methyltriazine (VI) yielding the bis-triazinyl piperazine (VII).Dehalogenation of (VII) by transfer hydrogenation with Pd/C and ammonium formate produces (VIII),which is finally subjected to methyl ether cleavage with BBr3 to furnish the title compound (1,2).
📌 参考资料/链接：
参考文献标题:Triazine cpds.useful as sorbitol dehydrogenase inhibitors
文献作者:Mylari,B.L.(Pfizer Products Inc.)
参考来源:EP 1247809
📄 详细内容
合成路线:Acylation of cis-2,6-dimethylpiperazine (I) with dimethylcarbamoyl chloride affords urea (II) (1,2).(R)-2-Methoxypropionamidine (III) is reacted with cyanogen bromide to produce the N-cyano amidine (IV) (1).Treatment of the carbamoyl piperazine (II) with POCl3,followed by condensation with cyanoamidine (IV) in refluxing acetonitrile gives rise to the piperazinyl triazine (V),which is condensed with 2,4-dichloro-6-methyltriazine (VI) yielding the bis-triazinyl piperazine (VII).Dehalogenation of (VII) by transfer hydrogenation with Pd/C and ammonium formate produces (VIII),which is finally subjected to methyl ether cleavage with BBr3 to furnish the title compound (1,2).
参考文献标题:Design and synthesis of a novel family of triazine-based inhibitors of sorbitol dehydrogenase with oral activity: 1-{4-[3R,5S-Dimethyl-4-(4-methyl-[1,3,5]triazin-2-yl)-piperazin-1-yl]-[1,3,5]triazin-2-yl}-(R) ethanol
文献作者:Mylari,B.L.; Withbroe,G.J.; Beebe,D.A.; Brackett,N.S.; Conn,E.L.; Coutcher,J.B.; Oates,P.J.; Zembrowski,W.J.
参考来源:Bioorg Med Chem 2003,11(19),4179