Reaktionsgleichung
[NH2:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[C:7]([NH2:9])=[O:8].[CH2:10]([C:14]1[NH:15][C:16]([Cl:21])=[C:17]([CH:19]=O)[N:18]=1)[CH2:11][CH2:12][CH3:13].[BH3-]C#N.[Na+].C(O)(=O)C>CO>[CH2:10]([C:14]1[NH:18][C:17]([CH2:19][NH:1][C:2]2[N:3]=[CH:4][NH:5][C:6]=2[C:7]([NH2:9])=[O:8])=[C:16]([Cl:21])[N:15]=1)[CH2:11][CH2:12][CH3:13]Komponenten
6
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A reaction mixture of 4-amino-5-imidazolecarboxamide (0.50 g, 3.96 mmol), 2-butyl-5-chloro-1H-imidazole-4-carbaldehyde (0.89 g, 4.76 mmol), and NaCNBH3 (0.25 g, 3.96 mmol) in methanol (5 mL) was stirred at r.t. over night. Acetic acid (0.24 g, 3.96 mmol) was added and the mixture was heated at 50° C. for 5 h. The mixture was concentrated in vacuo and dissolved in ethyl acetate and washed with water. The aqueous phase was extracted twice with ethyl acetate. The combined organic layers were dried (MgSO4) and concentrated. The crude product was purified by flash column chromatography (CH2Cl2/methanol gradient; 0 to 20% methanol), obtaining 0.30 g (26%) of the title compound.
Aufarbeitung
- temperaturethe mixture was heated at 50° C. for 5 h
- concentrationThe mixture was concentrated in vacuo
- dissolutiondissolved in ethyl acetate
- washwashed with water
- extractionThe aqueous phase was extracted twice with ethyl acetate
- dry with materialThe combined organic layers were dried (MgSO4)
- concentrationconcentrated
- customThe crude product was purified by flash column chromatography (CH2Cl2/methanol gradient; 0 to 20% methanol)
Quellen und Nachweise
- ORD-Eintrag
- ord-ef92e652f2bb4a359c25e63cdfca4f47
- Quelldatensatz
- uspto-grants-2011_09
- Patentnummer
- US08026244B2
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