Ammonia → 1-(4-Amino-2-(methoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol
Reaktionsgleichung
Cl[C:2]1[C:11]([NH:12][C:13](=O)[CH2:14]COC)=[C:10]([NH:19][CH2:20][C:21]([OH:24])([CH3:23])[CH3:22])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH3:25].[CH3:26][OH:27]>O.C(=O)(O)[O-].[Na+]>[NH2:25][C:2]1[C:11]2[N:12]=[C:13]([CH2:14][O:27][CH3:26])[N:19]([CH2:20][C:21]([CH3:22])([CH3:23])[OH:24])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1Komponenten
6
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 150 °C
Versuchsvorschrift
N-[2-Chloro-4-(2-hydroxy-2-methylpropyl)amino-3-quinolinyl]-3-methoxypropanamide (6 g, Example 110) was added to 5% ammonia in methanol (60 mL). The mixture was heated in a Parr bomb for 5 hours at approximately 150° C. The solvent was evaporated under vacuum to give a brown residue. The residue was diluted with water and sodium bicarbonate then extracted with ethyl acetate. The ethyl acetate extract was washed with water, dried over magnesium sulfate then evaporated to provide a tan solid. The solid was purified by silica gel chromatography to provide 1.64 g of the desired product as a solid, m.p. 174-175° C. Analysis: Calculated: %C, 65.0; %H, 7.0; %N, 17.8; Found: %C, 64.8; %H, 7.0; %N, 17.7.
Aufarbeitung
- customThe solvent was evaporated under vacuum
- customto give a brown residue
- extractionthen extracted with ethyl acetate
- extractionThe ethyl acetate extract
- washwas washed with water
- dry with materialdried over magnesium sulfate
- customthen evaporated
- customto provide a tan solid
- customThe solid was purified by silica gel chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-90ade706c9cf4ed2966ff32bd1917820
- Quelldatensatz
- uspto-grants-2003_08
- Patentnummer
- US06608201B2
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