新产品编号:865863
Chemical Name: 4-[2-Chloro-4-(trifluoromethoxy)phenyl]-2-ethyl-1-[1(S)-methylbutyl]-1H-imidazo[4,5-c]pyridine
CAS No. 345226-18-8 (undefined stereoch.)
项目整合开发状态: Preclinical
项目研究机构: Bristol-Myers Squibb (Originator)
合成路线:Chlorination of 4-(trifluoromethoxy)aniline (V) employing N-chlorosuccinimide affords the 2-chloro aniline (VI).Diazotization of aniline (VI) and subsequent quenching with potassium iodide gives rise to the aryl iodide (VII).This is converted into the arylboronic acid (VIII) by lithiation with butyllithium,followed by reaction with triisopropyl borate.Suzuki coupling between chloropyridine (IV) and boronic acid (VIII) leads to the phenylpyridine (IX).Reduction of the nitro group of (IX) employing sodium dithionite provides the diaminopyridine (X).This is finally condensed with triethyl orthopropionate to produce the target imidazopyridine compound.
📌 参考资料/链接：
参考文献标题:Imidazopyrimidinyl and imidazopyridinyl derivs.
文献作者:Wilde,R.G.; Bakthavatchalam,R.; Beck,J.P.; Arvanitis,A.(Bristol-Myers Squibb Co.)
参考来源:EP 1244666; JP 2003516992; WO 0144248
📄 详细内容
合成路线:4-Chloro-2-hydroxy-3-nitropyridine (I) is condensed with (S)-2-pentylamine (II) to produce the aminopyridine adduct (III).Subsequent chlorination of (III) by means of POCl3 furnishes the chloropyridine derivative (IV).
合成路线:Chlorination of 4-(trifluoromethoxy)aniline (V) employing N-chlorosuccinimide affords the 2-chloro aniline (VI).Diazotization of aniline (VI) and subsequent quenching with potassium iodide gives rise to the aryl iodide (VII).This is converted into the arylboronic acid (VIII) by lithiation with butyllithium,followed by reaction with triisopropyl borate.Suzuki coupling between chloropyridine (IV) and boronic acid (VIII) leads to the phenylpyridine (IX).Reduction of the nitro group of (IX) employing sodium dithionite provides the diaminopyridine (X).This is finally condensed with triethyl orthopropionate to produce the target imidazopyridine compound.
参考文献标题:Imidazo[4,5-c]pyridines as corticotropin releasing factor receptor ligands
文献作者:Arvanitis,A.G.; Rescinito,J.T.; Arnold,C.R.; Wilde,R.G.; Fitzgerald,L.W.; Zaczek,R.; Hartig,P.R.; Grossman,S.; Arneric,S.P.; Gilligan,P.J.; Olson,R.E.; Robertson,D.W.
参考来源:Bioorg Med Chem Lett 2003,13(1),129