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Resiquimod, VML-600, R-848, S-28463

雷西莫特Chemical Name: 1-[4-Amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol; 4-Amino-2-(ethoxymethyl)-alpha,alpha-dimethyl-1H-imidazo[4,5-c]quinoline-1-ethanol
CAS No. 144875-48-9
项目整合开发状态: Phase III
项目研究机构: 3M Pharmaceuticals (Originator), Lilly (Licensee)
合成路线:The esterification of 3-nitroquinoline-2,4-diol (I) with trifluoromethanesulfonic anhydride (II) gives the disulfonate (III),which is condensed with 2-hydroxyisobutylamine (IV) and triethylamine in dichloromethane,yielding the aminoquinoline (V).The reaction of (V) with dibenzylamine by means of triethylamine in refluxing toluene affords the quinolinediamine (VI),which by reduction of its nitro group with NaBH4 provides the quinolinetriamine (VII).The cyclization of (VII) with 2-ethoxyacetyl chloride (VIII) by means of p-toluenesulfonic acid in refluxing acetonitrile gives the protected imidazoquinoline (IX),which is finally deprotected by treatment with Pd/C and formic acid.
📌 参考资料/链接:
参考文献标题:1-Substd.,2-substd.1H-imidazo[4,5-c]quinolin-4-amines
文献作者:Gerster,J.F.; Crooks,S.L.; Lindstrom,K.J.(3M Pharmaceuticals)
参考来源:EP 0582581; JP 1994504789; US 5389640; WO 9215582

📄 详细内容


合成路线:The cyclization of the diaminoquinoline (I) with ethoxyacetic acid (II) by heating at 120 C gives the imidazoquinoline (III),which is oxidized to the 5-N-oxide (IV) by treatment with peracetic acid.Finally,compound (IV) is aminated by means of ammonium hydroxide and p-toluenesulfonyl chloride in dichloromethane.

参考文献标题:Process for preparing quinolone amines
文献作者:Nikolaides,N.; Lindstrom,K.J.(3M Pharmaceuticals)
参考来源:WO 9417043


合成路线:The esterification of 3-nitroquinoline-2,4-diol (I) with trifluoromethanesulfonic anhydride (II) gives the disulfonate (III),which is condensed with 2-hydroxyisobutylamine (IV) and triethylamine in dichloromethane,yielding the aminoquinoline (V).The reaction of (V) with dibenzylamine by means of triethylamine in refluxing toluene affords the quinolinediamine (VI),which by reduction of its nitro group with NaBH4 provides the quinolinetriamine (VII).The cyclization of (VII) with 2-ethoxyacetyl chloride (VIII) by means of p-toluenesulfonic acid in refluxing acetonitrile gives the protected imidazoquinoline (IX),which is finally deprotected by treatment with Pd/C and formic acid.

合成路线:The cyclization of the diaminoquinoline (I) with ethoxyacetic acid (II) by heating at 120 C gives the imidazoquinoline (III),which is oxidized to the 5-N-oxide (IV) by treatment with peracetic acid.Finally,compound (IV) is aminated by means of ammonium hydroxide and p-toluenesulfonyl chloride in dichloromethane.
参考文献标题:S-28463
文献作者:Graul,A.; Castar,J.
参考来源:Drugs Fut 1999,24(6),622


产品链接: CAS No. 144875-48-9››