Hydrogen Peroxide → (S)-6-(5-Cyclopropyl-1H-pyrazol-3-ylamino)-5-fluoro-2-(1-(4-fluorophenyl)ethylamino)nicotinamide
Reaktionsgleichung
[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[C:17]([F:18])=[CH:16][C:13]([C:14]#[N:15])=[C:12]([NH:19][C@H:20]([C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=4)[CH3:21])[N:11]=3)[CH:5]=2)[CH2:3][CH2:2]1.[OH-:29].[K+].OO>CO>[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[C:17]([F:18])=[CH:16][C:13]([C:14]([NH2:15])=[O:29])=[C:12]([NH:19][C@H:20]([C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=4)[CH3:21])[N:11]=3)[CH:5]=2)[CH2:3][CH2:2]1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 65 °C
Versuchsvorschrift
To a solution of (S)-6-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-fluoro-2-(1-(4-fluorophenyl)ethylamino)nicotinonitrile (Method 42; 0.5 g, 1.3 mmol) in MeOH (50 ml) was added KOH solution (25%, 2 ml), followed by addition of H2O2 (30%, 0.1 ml). The resulting dark red solution was heated to 65° C. for 1 hour, cooled, and concentrated. The resulting residue was dissolved in EtOAc (50 ml), washed with water (30 ml), dried, filtered, and concentrated. The resulting solid was purified by column chromatography (DCM:MeOH=30:1) to give the title compound (0.30 g, 60%). MS: Calcd.: 398. Found: [M+H]+ 399.
Aufarbeitung
- temperaturecooled
- concentrationconcentrated
- dissolutionThe resulting residue was dissolved in EtOAc (50 ml)
- washwashed with water (30 ml)
- customdried
- filtrationfiltered
- concentrationconcentrated
- customThe resulting solid was purified by column chromatography (DCM:MeOH=30:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-19f81edc12dd4983b673089763d9a7fe
- Quelldatensatz
- uspto-grants-2009_11
- Patentnummer
- US07622482B2
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