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Water → HCID 178446132, Verbindung

HRID 730008
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 730008
[C:1]([C:5]1[NH:9][C:8]([C:10]2[N:15]=[C:14]([NH:16][CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])[C:13]([N+:22]([O-])=O)=[CH:12][CH:11]=2)=[C:7]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[N:32]#[C:33]Br.C(OCC)(=O)C.O>[Pd].C(O)C.CO.C(Cl)Cl>[NH3:6].[C:1]([C:5]1[NH:6][C:7]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)=[C:8]([C:10]2[N:15]=[C:14]3[N:16]([CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])[C:33]([NH2:32])=[N:22][C:13]3=[CH:12][CH:11]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

10

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 10476Cyanogen BromideHCID 68867957HCID 68867957, Verbindung

Produkt 2

HCID 222AmmoniaHCID 178446132HCID 178446132, VerbindungAusbeute 74,2 %

Reagenzien, Katalysatoren, Lösungsmittel

4
HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittelHCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Stir a suspension of {6-[2-tert-Butyl-5-(4-fluoro-phenyl)-3H-imidazol-4-yl]-3-nitro-pyridin-2-yl}-(2,2-dimethylpropyl)-amine (426 mg, 1.0 mmol) and 10% palladium on carbon (85 mg) in 100% ethanol under hydrogen from a balloon overnight. Filter the suspension through a 0.2 μm syringe filter and concentrate under reduced pressure. Dissolve the residue in 10% aqueous ethanol and treat at room temperature with cyanogen bromide (80 mg, 0.75 mmol, 1.5 equiv). When the reaction is complete, quench the reaction with saturated aqueous NaHCO3. Add ethyl acetate and water to dissolve all solids. Wash the organic layer once with saturated aqueous NaHCO3, once with saturated aqueous NaCl, dry with Na2SO4, filter, and concentrate under reduced pressure. Subject the residue to medium pressure silica gel chromatography eluting with 50% ethyl acetate/CH2Cl2 then with a gradient of 1.5-3.5% (2M ammonia in MeOH)/CH2Cl2) to provide 5-[2-tert-butyl-5-(4-fluoro-phenyl)-1H-imidazol-4-yl]-3-(2,2-dimethyl-propyl)-3H-imidazo[4,5-b]pyridin-2-ylamine as a brown foam (156 mg, 74% yield).

Aufarbeitung

  1. filtrationFilter the suspension through a 0.2 μm syringe
  2. filtrationfilter
  3. concentrationconcentrate under reduced pressure
  4. dissolutionDissolve the residue in 10% aqueous ethanol
  5. customquench
  6. customthe reaction with saturated aqueous NaHCO3
  7. washWash the organic layer once with saturated aqueous NaHCO3
  8. dry with materialonce with saturated aqueous NaCl, dry with Na2SO4
  9. filtrationfilter
  10. concentrationconcentrate under reduced pressure
  11. washeluting with 50% ethyl acetate/CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-c2fe895bf56e4317a1c991fd8b31d2be
Quelldatensatz
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07582652B2

Notizen zur Reaktion

Wird geladen…

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