Chemical Name: 4-[2-(4-Chlorophenyl)-4-(2,4-dibutoxyphenyl)-1H-imidazol-5-yl]pyridine
CAS No. 208188-17-4 (tautomer)
项目整合开发状态: Biological Testing
项目研究机构: Merck & Co. (Originator)
合成路线:The reaction of 3,5-dihydroxybenzoic acid (I) with N,O-dimethylhydroxylamine (II) by means of EDC and NMM in dichloromethane gives the N,O-dimethylbenzamide (III),which is alkylated with butyl bromide (IV) and K2CO3 in hot DMF to yield the dibutoxybenzamide (V).The condensation of (V) with 4-methylpyridine (VI) by means of LDA in THF affords 1-(2,4-dibutoxyphenyl)-2-(4-pyridyl)ethanone (VII),which is oxidized with SeO2 in hot acetic acid to provide the dione (VIII).Finally,this compound is cyclized with 4-chlorobenzaldehyde (IX) and ammonium acetate in refluxing acetic acid to furnish the target imidazole.
📄 详细内容
合成路线:The reaction of 3,5-dihydroxybenzoic acid (I) with N,O-dimethylhydroxylamine (II) by means of EDC and NMM in dichloromethane gives the N,O-dimethylbenzamide (III),which is alkylated with butyl bromide (IV) and K2CO3 in hot DMF to yield the dibutoxybenzamide (V).The condensation of (V) with 4-methylpyridine (VI) by means of LDA in THF affords 1-(2,4-dibutoxyphenyl)-2-(4-pyridyl)ethanone (VII),which is oxidized with SeO2 in hot acetic acid to provide the dione (VIII).Finally,this compound is cyclized with 4-chlorobenzaldehyde (IX) and ammonium acetate in refluxing acetic acid to furnish the target imidazole.
参考文献标题:Selective,non-peptide antagonists for the glucagon receptor: Substituted imidazoles
文献作者:de Laszlo,S.; O'Keefe,S.; Li,B.; MacCoss,M.; Rolando,A.; mantlo,N.; Koch,G.; Cascieri,M.A.; Hagmann,W.K.; Chang,L.L.; Pang,M.; Sidler,K.L.
参考来源:221st ACS Natl Meet (April 1 2001,San Diego) 2001,Abst MEDI 237
合成路线:The reaction of 3,5-dihydroxybenzoic acid (I) with N,O-dimethylhydroxylamine (II) by means of EDC and NMM in dichloromethane gives the N,O-dimethylbenzamide (III),which is alkylated with butyl bromide (IV) and K2CO3 in hot DMF to yield the dibutoxybenzamide (V).The condensation of (V) with 4-methylpyridine (VI) by means of LDA in THF affords 1-(2,4-dibutoxyphenyl)-2-(4-pyridyl)ethanone (VII),which is oxidized with SeO2 in hot acetic acid to provide the dione (VIII).Finally,this compound is cyclized with 4-chlorobenzaldehyde (IX) and ammonium acetate in refluxing acetic acid to furnish the target imidazole.
参考文献标题:Substituted imidazoles as gluagon receptor antagonists
文献作者:Chang,L.L.; Sidler,K.L..; Cascieri,M.A.; de Laszlo,S.; Koch,G.; Li,B.; MacCoss,M.; mantlo,N.; O'Keefe,S.; Pang,M.; Rolando,A.; Hagmann,W.K.
参考来源:Bioorg Med Chem Lett 2001,11(18),2549