Triphosgene → HCID 24853021, Verbindung

HRID 551815Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 551815
[CH3:1][S:2]([C:5]1[CH:21]=[CH:20][C:8]([CH2:9][N:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][CH2:12][CH2:11]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].ClC(Cl)(O[C:26](=[O:32])OC(Cl)(Cl)Cl)Cl.Cl.Cl.[NH:36]1[CH2:40][CH2:39][CH:38]([C:41]2[CH:42]=[N:43][NH:44][CH:45]=2)[CH2:37]1.C(=O)([O-])O.[Na+]>ClCCl.CN1CCOCC1.O>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][N:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]([C:26]([N:36]3[CH2:40][CH2:39][CH:38]([C:41]4[CH:42]=[N:43][NH:44][CH:45]=4)[CH2:37]3)=[O:32])[CH2:12][CH2:11]2)=[CH:20][CH:21]=1)(=[O:3])=[O:4]

Komponenten

8

Edukt 4

HCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 671872294-(pyrrolidin-3-yl)-1H-pyrazole dihydrochlorideHCID 67190176HCID 67190176, Verbindung

Produkt 1

HCID 24853021HCID 24853021, VerbindungAusbeute 34,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×HCID 79724-MethylmorpholineLösungsmittel

Versuchsvorschrift

0.3 g of 4-(4-(methanesulfonyl)benzyl)-3,4-dihydro-2H-quinoxaline is dissolved in 10 ml of dichloromethane and 0.1 ml of N-methylmorpholine. 0.118 g of triphosgene is added at 0° C. and then the reaction mixture is left stirring at ambient temperature for four hours. 0.208 g of 4-(pyrrolidin-3-yl)-1H-pyrazole dihydrochloride is subsequently added and the reaction mixture is stirred for eighteen hours. A saturated solution of sodium hydrogencarbonate in water and dichloromethane are added. The aqueous phase is extracted twice with dichloromethane. The organic phases are combined, washed with water and with a saturated aqueous sodium chloride solution and dried over magnesium sulfate and then the solvent is evaporated under reduced pressure. The residue is chromatographed on silica gel, a first time with a gradient of dichloromethane/methanol 1/0 to 85/5 mixture and then a second time with a gradient of dichloromethane/ethyl acetate/methanol 1/0/0 to 70/25/5 mixture. 0.064 g of [4-(4-(methanesulfonyl)benzyl)-3,4-dihydro-2H-quinoxalin-1-yl][3-(1H-pyrazol-4-yl)pyrrolidin-1-yl]methanone is obtained.

Aufarbeitung

  1. waitthe reaction mixture is left
  2. stirringthe reaction mixture is stirred for eighteen hours
  3. extractionThe aqueous phase is extracted twice with dichloromethane
  4. washwashed with water and with a saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent is evaporated under reduced pressure
  7. customThe residue is chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-69b2f4177485470f923cd30c240587f0
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947834B2

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