Pyridinium hydrochloride → 4-{8-[4-(4-Methylpiperazin-1-yl)phenylamino]imidazo[1,2-a]pyrazin-5-yl}-1H-pyridin-2-one
Reaktionsgleichung
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]3[C:16]4[N:17]([CH:30]=[CH:31][N:32]=4)[C:18]([C:21]4[CH:26]=[CH:25][N:24]=[C:23]([O:27]CC)[CH:22]=4)=[CH:19][N:20]=3)=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.Cl.[NH+]1C=CC=CC=1>O>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[CH:10][C:11]([NH:14][C:15]3[C:16]4[N:17]([CH:30]=[CH:31][N:32]=4)[C:18]([C:21]4[CH:26]=[CH:25][NH:24][C:23](=[O:27])[CH:22]=4)=[CH:19][N:20]=3)=[CH:12][CH:13]=2)[CH2:4][CH2:3]1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 150 °C
Versuchsvorschrift
A mixture of (4-(4-methylpiperazin-1-yl)phenyl)-[5-(2-ethoxypyridin-4-yl)-imidazo[1,2-a]pyrazin-8-yl]amine (103 mg, 0.24 mmol) and pyridinium hydrochloride (130 mg, 1.2 mmol) in water (0.2 mL) is heated at 150° C. for 25 minutes in a sealed tube. After this time the solvent is removed in vacuo. The residue is chromatographed on silica gel, eluting with DCM followed by 92:8 DCM:NH3 (7M in MeOH), and the fractions containing the desired product are combined and evaporated to afford the title compound as a solid. HPLC (254 nm): Rt 1.70 min (99.7%); m/z (APCI) 402 (M+H)+.
Aufarbeitung
- customAfter this time the solvent is removed in vacuo
- customThe residue is chromatographed on silica gel
- washeluting with DCM
- additionNH3 (7M in MeOH), and the fractions containing the desired product
- customevaporated
Quellen und Nachweise
- ORD-Eintrag
- ord-18b3f5709fd34197bc0b013f64f90758
- Quelldatensatz
- uspto-grants-2011_02
- Patentnummer
- US07893058B2
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