Oxalyl chloride → 1-Cyclopropyl-3-(2,6-dichloro-5-fluoro-pyridine-3-carbonyl)urea
Reaktionsgleichung
[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[C:13](Cl)(=[O:17])C(Cl)=O.[CH:19]1([NH2:22])[CH2:21][CH2:20]1>ClCCl>[CH:19]1([NH:22][C:13]([NH:6][C:4]([C:3]2[C:2]([Cl:1])=[N:10][C:9]([Cl:11])=[C:8]([F:12])[CH:7]=2)=[O:5])=[O:17])[CH2:21][CH2:20]1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -20 °C
Versuchsvorschrift
A solution of 5.8 g (27.8 mmol) of 2,6-dichloro-5-fluoronicotinamide (Chem. Pharm. Bull., 1987; 35:2280) in 60 mL of dichloromethane is treated dropwise with 5.1 g (40 mmol) of oxalyl chloride, and the reaction mixture is heated at reflux for 18 hours. The solvent is removed in vacuo, and the residue is dissolved in 50 mL of dichloromethane, which is also removed in vacuo. The residue is dissolved in 50 mL of dichloromethane, cooled to −20° C. and treated dropwise with 2.28 g (40 mmol) of cyclopropylamine. The reaction mixture is stirred at −20° to −10° C. for ½ hour, then allowed to come to room temperature over 2 hours. The solvent is removed in vacuo and the residue is triturated with 25 mL of dichloromethane, which is also removed in vacuo to give 8.0 g of the title compound, mp 171–173° C.
Aufarbeitung
- temperaturethe reaction mixture is heated
- temperatureat reflux for 18 hours
- customThe solvent is removed in vacuo
- dissolutionthe residue is dissolved in 50 mL of dichloromethane
- customwhich is also removed in vacuo
- dissolutionThe residue is dissolved in 50 mL of dichloromethane
- waitto come to room temperature over 2 hours
- customThe solvent is removed in vacuo
- customthe residue is triturated with 25 mL of dichloromethane, which
- customis also removed in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-950eac8099204e9080cda488ff8ca284
- Quelldatensatz
- uspto-grants-2006_08
- Patentnummer
- US07094780B1
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