Reaktionsgleichung
[CH2:1]([O:4][CH2:5][CH2:6][N:7]1[C:19]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=[C:11]([NH2:20])[C:10]=2[N:9]=[CH:8]1)[C:2]#[CH:3].[C:21]1([O:27][C:28]2[CH:33]=[CH:32][C:31](I)=[CH:30][CH:29]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[OH-].[Na+]>>[O:27]([C:28]1[CH:29]=[CH:30][C:31]([C:3]#[C:2][CH2:1][O:4][CH2:5][CH2:6][N:7]2[C:19]3[C:18]4[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=4[N:12]=[C:11]([NH2:20])[C:10]=3[N:9]=[CH:8]2)=[CH:32][CH:33]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1Komponenten
4
Versuchsvorschrift
Using the general method of Example 7, 1-[2-(2-propynyloxy)ethyl]-1H-imidazo[4,5-c]quinolin-4-amine (0.50 g, 1.88 mmol) was reacted with 4-iodophenyl phenyl ether (0.78 g, 2.63 mmol). The crude product was purified by column chromatography eluting with 95/5 dichloromethane/methanol to provide a solid. The solid was slurried with aqueous sodium hydroxide to remove salts and then purified by column chromatography eluting with 9/1 ethyl acetate/methanol to provide a solid. This material was further purified by column chromatography eluting with 99/1 ethyl acetate/methanol to provide 24 mg of 1-(2-{[3-(4-phenoxyphenyl)-2-propynyl]oxy}ethyl)-1H-imidazo[4,5-c]quinolin-4-amine as a solid, m.p. 146-148° C.
Aufarbeitung
- customThe crude product was purified by column chromatography
- washeluting with 95/5 dichloromethane/methanol
- customto provide a solid
- customto remove salts
- custompurified by column chromatography
- washeluting with 9/1 ethyl acetate/methanol
- customto provide a solid
- customThis material was further purified by column chromatography
- washeluting with 99/1 ethyl acetate/methanol
Quellen und Nachweise
- ORD-Eintrag
- ord-35b37ff3b9614f59a46df081fc35399c
- Quelldatensatz
- uspto-grants-2003_12
- Patentnummer
- US06670372B2
Verknüpfte Notizen
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