Imidazole → [5-(2-Imidazol-1-yl-pyridin-4-yl)-4-methyl-thiazol-2-yl]-pyrazin-2-yl-amine
Reaktionsgleichung
Cl[C:2]1[CH:7]=[C:6]([C:8]2[S:12][C:11]([NH:13][C:14]3[CH:19]=[N:18][CH:17]=[CH:16][N:15]=3)=[N:10][C:9]=2[CH3:20])[CH:5]=[CH:4][N:3]=1.[NH:21]1[CH:25]=[CH:24][N:23]=[CH:22]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.O>[N:21]1([C:2]2[CH:7]=[C:6]([C:8]3[S:12][C:11]([NH:13][C:14]4[CH:19]=[N:18][CH:17]=[CH:16][N:15]=4)=[N:10][C:9]=3[CH3:20])[CH:5]=[CH:4][N:3]=2)[CH:25]=[CH:24][N:23]=[CH:22]1Komponenten
6
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 140 °C
Versuchsvorschrift
A stirred solution of [5-(2-Chloro-pyridin-4-yl)-4-methyl-thiazol-2-yl]-pyrazin-2-yl-amine (Ex. 2b, 0.4 g, 1.32 mmol) in DMSO (10 ml) is treated with imidazole (0.18 g, 2.64 mmol) followed by caesium carbonate (0.86 g, 2.64 mmol). The reaction mixture is heated to 140° C. for 48 hours and then allowed to cool to room temperature. The mixture is diluted with water (100 ml) and extracted with ethyl acetate (4×100 ml). The organics are combined, dried over MgSO4 and the solvent removed in vacuo to yield the crude product as a yellow oil. Purification by chromatography on silica, eluting with ethyl acetate-methanol (9:1) affords the titled compound.
Aufarbeitung
- temperatureto cool to room temperature
- extractionextracted with ethyl acetate (4×100 ml)
- dry with materialdried over MgSO4
- customthe solvent removed in vacuo
- customto yield the crude product as a yellow oil
- customPurification by chromatography on silica
- washeluting with ethyl acetate-methanol (9:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-836e663510a7495d90d78c935f503d1f
- Quelldatensatz
- uspto-grants-2013_03
- Patentnummer
- US08404684B2
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