ABT-702
5-(3-溴苯基)-7-[6-(4-吗啉基)-3-吡啶基]-吡啶并[2,3-d]嘧啶-4-胺Chemical Name: 5-(3-Bromophenyl)-7-[6-(4-morpholinyl)pyridin-3-yl]pyrido[2,3-d]pyrimidin-4-amine; 5-(3-Bromophenyl)-7-[6-(4-morpholinyl)pyridin-3-yl]pyrido[2,3-d]pyrimidin-4-ylamine
CAS No. 214697-26-4
项目整合开发状态: Preclinical
项目研究机构: Abbott (Originator)
合成路线:The condensation between 3-bromobenzaldehyde (I),1-(6-morpholinyl-3-pyridinyl)ethanone (II) and malononitrile in the presence of ammonium acetate in refluxing benzene produced the bipyridyl derivative (III).Then treatment of (III) with refluxing formamide gave the title pyridopyrimidine.
📌 参考资料/链接：
参考文献标题:5,7-Disubstd.-4-aminopyrido[2,3-d]pyrimidine cpds.and their use as adenosine kinase inhibitors
文献作者:Cowart,M.D.; Lee,C.-H.; Grillot,A.L.; Bhagwat,S.S.; McKie,J.(Abbott Laboratories Inc.)
参考来源:EP 0989986; WO 9846605
📄 详细内容
合成路线:The condensation between 3-bromobenzaldehyde (I),1-(6-morpholinyl-3-pyridinyl)ethanone (II) and malononitrile in the presence of ammonium acetate in refluxing benzene produced the bipyridyl derivative (III).Then treatment of (III) with refluxing formamide gave the title pyridopyrimidine.
合成路线:6-Chloronicotinic acid (I) was converted to the corresponding acid chloride (II) by treatment with oxalyl chloride.Condensation of acid chloride (II) with diethyl malonate in the presence of MgCl2 and Et3N produced the keto diester (III),which was further decarbethoxylated to ketone (IV) upon heating in moist DMSO.Displacement of the chloride group of (III) with 4-piperidone ethylene ketal (V) furnished the piperidinyl pyridine (VI).Knoevenagel condensation of malononitrile with 3-bromobenzaldehyde (VII) using glycine as the catalyst produced the benzylidene malononitrile (VIII).The dipyridyl derivative (IX) was obtained by condensation of ketone (VI) with dinitrile (VIII) in the presence of ammonium acetate.Cyclization of amino nitrile (IX) in hot formamide gave rise to the pyridopyrimidine system (X).Ketone (XI) was then obtained by acid hydrolysis of the ethylene ketal function of (X).Finally,condensation of ketone (XI) with 4-tetrahydropyranyloxyamine (XII) yielded the title oxime.
参考文献标题:5,7-Disubstd.-4-aminopyrido[2,3-d]pyrimidine cpds.
文献作者:Stewart,A.O.; Perner,R.J.; McKie,J.A.; Zheng,G.Z.; Grillot,A.L.; Cowart,M.D.; Bhagwat,S.S.; Lee,C.-H.(Abbott Laboratories Inc.)
参考来源:WO 0023444
合成路线:The condensation between 3-bromobenzaldehyde (I),1-(6-morpholinyl-3-pyridinyl)ethanone (II) and malononitrile in the presence of ammonium acetate in refluxing benzene produced the bipyridyl derivative (III).Then treatment of (III) with refluxing formamide gave the title pyridopyrimidine.
参考文献标题:Discovery of 4-amino-5-(3-bromophenyl)-7-(6-morpholino-pyridin-3-yl) pyrido[2,3-d]pyrimidine,an orally active,non-nucleoside adenosine kinase inhibitor
文献作者:Lee,C.-H.; Jiang,M.; Cowart,M.; Gfesser,G.; Perner,R.; Kim,K.H.; Gu,Y.G.; Williams,M.; Jarvis,M.F.; Kowaluk,E.A.; Stewart,A.O.; Bhagwat,S.S.
参考来源:J Med Chem 2001,44(13),2133
产品链接: CAS No. 214697-26-4››