Dimethylformamide → (R)-N-(benzoyl)-3-methyl-N'-[(1-methyl-7-azaindol-3-yl)-oxoacetyl]-piperazine

HRID 987540Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 987540
[H-].[Na+].[C:3]([N:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:29])[C:18]([C:20]2[C:28]3[C:23](=[N:24][CH:25]=[CH:26][CH:27]=3)[NH:22][CH:21]=2)=[O:19])[C@H:13]([CH3:30])[CH2:12]1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:31]N(C=O)C>>[C:3]([N:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:29])[C:18]([C:20]2[C:28]3[C:23](=[N:24][CH:25]=[CH:26][CH:27]=3)[N:22]([CH3:31])[CH:21]=2)=[O:19])[C@H:13]([CH3:30])[CH2:12]1)(=[O:10])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Komponenten

4

Edukt 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 5495793Piperazine, 4-benzoyl-1-(1,2-dioxo-2-(1H-pyrrolo(2,3-b)pyridin-3-yl)ethyl)-2-methyl-, (2R)-

Produkt 1

HCID 507780(R)-N-(benzoyl)-3-methyl-N'-[(1-methyl-7-azaindol-3-yl)-oxoacetyl]-piperazineAusbeute 24 %

Versuchsvorschrift

NaH (2 mg, 60% pure, 0.05 mmol) was added to a solution of compound 5a (10 mg, 0.027 mmol) in DMF. After 30 minutes, Mel (5 mg, 0.035 mmol) was injected into the mixture via syringe. The reaction mixture was stirred for 8 hours at room temperature and quenched with methanol. The mixture was partitioned between ethyl acetate (2 ml) and H2O (2 ml). The aqueous phase was extracted with EtOAc (3×2 ml). The organic layers were combined, dried over anhydrous MgSO4 and concentrated in vacuo to give a crude product which was purified using a Shimadzu automated preparative HPLC System to give compound 21a (2.5 mg, 24%).

Aufarbeitung

  1. customMel (5 mg, 0.035 mmol) was injected into the mixture via syringe
  2. customquenched with methanol
  3. customThe mixture was partitioned between ethyl acetate (2 ml) and H2O (2 ml)
  4. extractionThe aqueous phase was extracted with EtOAc (3×2 ml)
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated in vacuo
  7. customto give a crude product which
  8. customwas purified

Quellen und Nachweise

ORD-Eintrag
ord-36339e7d9ae9417b966d01d5181367b2
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06632819B1

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