Triethylamine → 4-{[4,5-Bis(3-chlorophenyl)furan-2-yl]carbonyl}piperazin-2-one
Reaktionsgleichung
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([C:20](O)=[O:21])[O:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=2)[CH:5]=[CH:6][CH:7]=1.S(Cl)(Cl)=O.C(N(CC)CC)C.[NH:34]1[CH2:39][CH2:38][NH:37][CH2:36][C:35]1=[O:40]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([C:20]([N:37]3[CH2:38][CH2:39][NH:34][C:35](=[O:40])[CH2:36]3)=[O:21])[O:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=2)[CH:5]=[CH:6][CH:7]=1Komponenten
6
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
600 mg (1.07 mmol) of the compound from Example 25A are provided in 14 ml of dry toluene, 0.24 ml (3.22 mmol) of thionyl chloride are added and the mixture is heated under reflux for 2.5 hours. The reaction mixture is concentrated, and the residue is taken up in 10 ml of dichloromethane and cooled to 0° C. 0.24 ml (1.72 mmol) of triethylamine and then 172 mg (1.72 mmol) of piperazin-2-one are then added, and the reaction mixture is stirred at RT overnight. The mixture is subsequently concentrated and the residue is purified by preparative HPLC (RP18 column; eluent: acetonitrile/water gradient). 302 mg (68% of theory) of the title compound are obtained.
Aufarbeitung
- temperaturethe mixture is heated
- temperatureunder reflux for 2.5 hours
- concentrationThe reaction mixture is concentrated
- concentrationThe mixture is subsequently concentrated
- customthe residue is purified by preparative HPLC (RP18 column; eluent: acetonitrile/water gradient)
Quellen und Nachweise
- ORD-Eintrag
- ord-a7ce85e68c684580bc85b092a83f9487
- Quelldatensatz
- uspto-grants-2012_12
- Patentnummer
- US08324268B2
Notizen zur Reaktion
Wird geladen…