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Chinoin-1045, UCB-L-140

Chemical Name: (+)-6,7,8,9-Tetrahydro-6-methyl-4-oxo-9-(phenylhydrazono)-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid
CAS No. 70999-42-7
项目整合开发状态: Biological Testing
项目研究机构: Chinoin (Originator), UCB (Originator)
合成路线:This compound can be obtained by several different ways:1) By condensation of 9,9-dibromo-6-methyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-3-carboxylic acid (I) with phenylhydrazine (II) by means of N,N-dimethylaniline in DMSO.2) By a coupling reaction between 6-methyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-3-carboxylic acid (III) with phenyldiazonium chloride (IV) (prepared with aniline (V),NaNO2 and HCl).3) The coupling reaction of (IV) with ethyl 6-methyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine 3-carboxylate (VI) gives ethyl 6-methyl-4-oxo-9-(phenylhydrazono)-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-3-carboxylate (VII),which is hydrolyzed with NaOH in water.4) By reaction of ethyl 9-bromo-6-methyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-3-carboxylate (VIII) with (II) in refluxing ethanol,giving (VII),already obtained.5) By condensation of ethyl 9-hydroxy-6-methyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-3-carboxylate (IX) with (II) in refluxing ethanol yielding (VII),already obtained.
📌 参考资料/链接:
参考文献标题:9-Hydrazono-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]-pyrimidine-4-one derivs.,their preparation and pharmaceutical compsns.containing them
文献作者:Vasvari,L.; Horvath,A.; Hermecz,I.; Kokosi,J.; Breining,T.(Chinoin Pharmaceutical and Chemical Works Co.,Ltd.)
参考来源:GB 2051783

📄 详细内容


合成路线:This compound can be obtained by several different ways:1) By condensation of 9,9-dibromo-6-methyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-3-carboxylic acid (I) with phenylhydrazine (II) by means of N,N-dimethylaniline in DMSO.2) By a coupling reaction between 6-methyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-3-carboxylic acid (III) with phenyldiazonium chloride (IV) (prepared with aniline (V),NaNO2 and HCl).3) The coupling reaction of (IV) with ethyl 6-methyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine 3-carboxylate (VI) gives ethyl 6-methyl-4-oxo-9-(phenylhydrazono)-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-3-carboxylate (VII),which is hydrolyzed with NaOH in water.4) By reaction of ethyl 9-bromo-6-methyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-3-carboxylate (VIII) with (II) in refluxing ethanol,giving (VII),already obtained.5) By condensation of ethyl 9-hydroxy-6-methyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-3-carboxylate (IX) with (II) in refluxing ethanol yielding (VII),already obtained.

参考文献标题:Condensed pyrimidine derivs.,their preparation and pharmaceutical compsns.containing them
文献作者:Bitter,I.; Breining,T.; Mandi,A.; Szucs,T.; Horvath,A.; Meszaros,Z.; Virag,S.; Hermecz,I.; Vasvari,L.; Nagy,G.; Sebestyen,G.(Chinoin Pharmaceutical and Chemical Works Co.,Ltd.)
参考来源:GB 2011898


合成路线:This compound can be obtained by several different ways:1) By condensation of 9,9-dibromo-6-methyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-3-carboxylic acid (I) with phenylhydrazine (II) by means of N,N-dimethylaniline in DMSO.2) By a coupling reaction between 6-methyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-3-carboxylic acid (III) with phenyldiazonium chloride (IV) (prepared with aniline (V),NaNO2 and HCl).3) The coupling reaction of (IV) with ethyl 6-methyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine 3-carboxylate (VI) gives ethyl 6-methyl-4-oxo-9-(phenylhydrazono)-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-3-carboxylate (VII),which is hydrolyzed with NaOH in water.4) By reaction of ethyl 9-bromo-6-methyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-3-carboxylate (VIII) with (II) in refluxing ethanol,giving (VII),already obtained.5) By condensation of ethyl 9-hydroxy-6-methyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-3-carboxylate (IX) with (II) in refluxing ethanol yielding (VII),already obtained.

参考文献标题:UCB-L-140
文献作者:Castar,J.; Serradell,M.N.; Sneddon,J.M.; Blancafort,P.
参考来源:Drugs Fut 1983,8(7),612


合成路线:This compound can be obtained by several different ways:1) By condensation of 9,9-dibromo-6-methyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-3-carboxylic acid (I) with phenylhydrazine (II) by means of N,N-dimethylaniline in DMSO.2) By a coupling reaction between 6-methyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-3-carboxylic acid (III) with phenyldiazonium chloride (IV) (prepared with aniline (V),NaNO2 and HCl).3) The coupling reaction of (IV) with ethyl 6-methyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine 3-carboxylate (VI) gives ethyl 6-methyl-4-oxo-9-(phenylhydrazono)-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-3-carboxylate (VII),which is hydrolyzed with NaOH in water.4) By reaction of ethyl 9-bromo-6-methyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-3-carboxylate (VIII) with (II) in refluxing ethanol,giving (VII),already obtained.5) By condensation of ethyl 9-hydroxy-6-methyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-3-carboxylate (IX) with (II) in refluxing ethanol yielding (VII),already obtained.
参考文献标题:18.New antiallergic 4H-pyridol[1,2-a]pyrimidin-4-ones
文献作者:Hermecz,I.; Breining,T.; M閟z醨os,Z.; Horv醫h,A.; Vasv醨i-Debreczy,L.; Dessy,F.; De Vos,C.; Rodr韌uez,L.
参考来源:J Med Chem 1982,25(10),1140-45


产品链接: CAS No. 70999-42-7››