Sodium Carbonate → HCID 44186480, Verbindung

HRID 42186

Reaktionsgleichung

Reaktionsgleichung von HRID 42186
C([O-])([O-])=O.[Na+].[Na+].Cl[C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][N:9]=1.[CH2:16]([C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26]([N:33]2[CH2:38][CH2:37][NH:36][C@H:35]([CH3:39])[CH2:34]2)=[N:25][N:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C=O)C.O1CCOCC1>[CH2:16]([C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26]([N:33]2[CH2:38][CH2:37][N:36]([C:8]3[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][N:9]=3)[C@H:35]([CH3:39])[CH2:34]2)=[N:25][N:24]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 51520946-Chloro-3-pyridinecarbonitrileHCID 441862481-Benzyl-4-((R)-3-methyl-piperazin-1-yl)-phthalazine

Produkt 1

HCID 44186480HCID 44186480, VerbindungAusbeute 42,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Solid Na2CO3 (50 mg, 0.47 mmol, 1.5 eq) is added to a solution of 6-chloronicotinonitrile (50 mg, 0.36 mmol, 1.2 eq), 1-benzyl-4-((R)-3-methyl-piperazin-1-yl)-phthalazine (100 mg, 0.31 mmol, 1.0 eq) in DMF (1 mL) and dioxane (2 mL) in a microwave vial. The vial is sealed and irradiated in the microwave at 180° C. (high absorption setting) for 30 minutes. The reaction mixture is concentrated, dichloromethane is added and is washed with water then brine. The organic fraction is dried over sodium sulfate, and is evaporated under reduced pressure, then purified by flash chromatography (50%-90% EtOAc/Hexane) to afford the title compound as a white solid (55 mg, 42% yield).

Aufarbeitung

  1. customThe vial is sealed
  2. customirradiated in the microwave at 180° C. (high absorption setting) for 30 minutes
  3. concentrationThe reaction mixture is concentrated
  4. additiondichloromethane is added
  5. washis washed with water
  6. dry with materialThe organic fraction is dried over sodium sulfate
  7. customis evaporated under reduced pressure
  8. custompurified by flash chromatography (50%-90% EtOAc/Hexane)

Quellen und Nachweise

ORD-Eintrag
ord-0ba5931c41c24e159e704285350d2dc6
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536168B2

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