CHIR-99021
6-[[2-[[4-(2,4-二氯苯基)-5-(5-甲基-1H-咪唑-2-基)-2-嘧啶]氨基]乙基]氨基]-3-吡啶甲腈Chemical Name: 6-[2-[4-(2,4-Dichlorophenyl)-5-(4-methyl-1H-imidazol-2-yl)pyrimidin-2-ylamino]ethylamino]pyridine-3-carbonitrile
CAS No. 252917-06-9
项目整合开发状态: Preclinical
项目研究机构: Chiron (Originator)
合成路线:Acylation of 2,4-dimethylimidazole (I) with 2,4-dichlorobenzoyl chloride (II) in the presence of diisopropylethylamine,followed by acidic hydrolysis,provides the 2-imidazolyl acetophenone (III).Subsequent condensation of (III) with dimethylformamide dimethylacetal gives rise to the enaminone (IV)
合成路线:Condensation of 2-chloro-5-cyanopyridine (V) with ethylenediamine (VI) yields the N-pyridyl ethylenediamine (VII).Subsequent reaction of amine (VII) with pyrazole-1-carboxyamidine (VIII) in refluxing acetonitrile affords guanidine (IX).Finally,condensation between guanidine (IX) and enaminone (IV) in the presence of NaOEt produces the title pyrimidine derivative
📌 参考资料/链接：
参考文献标题:Inhibitors of glycogen synthase kinase 3
文献作者:Brown,S.P.; Goff,D.; Ring,D.B.; Harrison,S.D.; Subramanian,S.; Nuss,J.M.; Boyce,R.S.; Johnson,K.; Pfister,K.B.; Ramurthy,S.; Renhowe,P.A.; Seely,L.; Wagman,A.S.; Zhou,X.A.(Chiron Corp.)
参考来源:EP 1087963; US 6417185; WO 9965897
📄 详细内容
合成路线:Acylation of 2,4-dimethylimidazole (I) with 2,4-dichlorobenzoyl chloride (II) in the presence of diisopropylethylamine,followed by acidic hydrolysis,provides the 2-imidazolyl acetophenone (III).Subsequent condensation of (III) with dimethylformamide dimethylacetal gives rise to the enaminone (IV)
合成路线:Condensation of 2-chloro-5-cyanopyridine (V) with ethylenediamine (VI) yields the N-pyridyl ethylenediamine (VII).Subsequent reaction of amine (VII) with pyrazole-1-carboxyamidine (VIII) in refluxing acetonitrile affords guanidine (IX).Finally,condensation between guanidine (IX) and enaminone (IV) in the presence of NaOEt produces the title pyrimidine derivative
参考文献标题:Inhibitors of glycogen synthase kinase 3
文献作者:Ring,D.B.; Harrison,S.D.; Nuss,J.M.; Boyce,R.S.; Johnson,K.; Pfister,K.B.; Ramurthy,S.; Seely,L.; Wagman,A.S.; Desai,M.; Levine,B.H.(Chiron Corp.)
参考来源:WO 0220495
产品链接: CAS No. 252917-06-9››