5-Amino-2-(piperidin-1-yl)benzonitrile → N-(3-Cyano-4-piperidinophenyl)-1,5-dimethylpyrazole-4-carboxamide
Reaktionsgleichung
[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([C:8]([OH:10])=O)[CH:4]=[N:3]1.ON1C2C=CC=CC=2N=N1.[NH2:21][C:22]1[CH:23]=[CH:24][C:25]([N:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)=[C:26]([CH:29]=1)[C:27]#[N:28]>C(O)C>[C:27]([C:26]1[CH:29]=[C:22]([NH:21][C:8]([C:5]2[CH:4]=[N:3][N:2]([CH3:1])[C:6]=2[CH3:7])=[O:10])[CH:23]=[CH:24][C:25]=1[N:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1)#[N:28]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 78 °C
Versuchsvorschrift
1-Hydroxybenzotriazole 1,5-dimethylpyrazole-4-carboxylate (1.2 g) and 5-amino-2-piperidinobenzonitrile (0.9 g) were added to ethanol (20 ml) and the mixture was stirred at 78° C. for 3 h. After evaporation of the solvent, aqueous potassium carbonate solution was added to the residue and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, after which the solvent was evaporated under reduced pressure. n-Hexane was added to the residue to allow crystallization. The crystals were recrystallized from hydrous ethanol to give the title compound (0.7 g), melting point: 217–218° C.
Aufarbeitung
- customAfter evaporation of the solvent, aqueous potassium carbonate solution
- additionwas added to the residue
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- customafter which the solvent was evaporated under reduced pressure
- additionn-Hexane was added to the residue
- customcrystallization
- customThe crystals were recrystallized from hydrous ethanol
Quellen und Nachweise
- ORD-Eintrag
- ord-21eeb7599b8c4d37a0462f8b5b9a2398
- Quelldatensatz
- uspto-grants-2006_03
- Patentnummer
- US07015218B1
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