FK-838
4-[6-氧代-3-(2-苯基吡唑并[1,5-a]吡啶-3-基)哒嗪-1-基]丁酸Chemical Name: 3-[2-(3-Carboxypropyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine; 4-[6-Oxo-3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-1,6-dihydropyridazin-1-yl]butyric acid
CAS No. 131185-37-0
项目整合开发状态: Phase II
项目研究机构: Fujisawa (Originator)
合成路线:The Grignard condensation of phenylethynylmagnesium bromide with acetic anhydride in THF gives 4-phenyl-3-butyn-2-one (II),which is cyclized with 1-aminopyridinium iodide (III) by means of KOH in dichloromethane yielding the pyrazolopyridine (IV).The reaction of (IV) with 2-oxoacetic acid (V) by means of acetic acid in dimethoxyethane (DME) affords the butyric acid derivative (VI),which is cyclized with hydrazine in hot DMA to give the pyridazinone (VII).The condensation of (VII) with 4-bromobutyric acid ethyl ester (VIII) by means of benzyltriethylammonium chloride in hot DME/methanol provides the butyric ester intermediate (IX),which is finally hydrolyzed with NaOH.
📌 参考资料/链接：
参考文献标题:Efficient large-scale synthesis of 4-phenyl-3-butyn-2-one,a key intermediate for a novel potent adenosine antagonist
文献作者:Zanka,A.
参考来源:Org Process Res Dev 1998,2(1),60
📄 详细内容
合成路线:The Grignard condensation of phenylethynylmagnesium bromide with acetic anhydride in THF gives 4-phenyl-3-butyn-2-one (II),which is cyclized with 1-aminopyridinium iodide (III) by means of KOH in dichloromethane yielding the pyrazolopyridine (IV).The reaction of (IV) with 2-oxoacetic acid (V) by means of acetic acid in dimethoxyethane (DME) affords the butyric acid derivative (VI),which is cyclized with hydrazine in hot DMA to give the pyridazinone (VII).The condensation of (VII) with 4-bromobutyric acid ethyl ester (VIII) by means of benzyltriethylammonium chloride in hot DME/methanol provides the butyric ester intermediate (IX),which is finally hydrolyzed with NaOH.
参考文献标题:Pilot-scale synthesis of a novel non-xanthine adenosine A1 receptor antagonist.1,3-dipolar cycloaddition of pyridine N-immine to an acetylene
文献作者:Zanka,A.; et al.
参考来源:Org Process Res Dev 1998,2(5),320
产品链接: CAS No. 131185-37-0››