1,1'-Carbonyldiimidazole → HCID 178446212, Verbindung

HRID 2262675Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2262675
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][CH:10]([CH2:13][CH3:14])[CH2:11][CH3:12])[C:5]([NH2:8])=[N:6][CH:7]=1.C1N=CN([C:20](N2C=NC=C2)=[O:21])C=1>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[N:9]([CH:10]([CH2:13][CH3:14])[CH2:11][CH3:12])[C:20]([OH:21])=[N:8][C:5]2=[N:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 682631,1'-Carbonyldiimidazole2×HCID 59594561HCID 59594561, Verbindung

Produkt 1

HCID 178446212HCID 178446212, VerbindungAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a refluxing solution of 5-chloro-N3-(pentan-3-yl)pyridine-2,3-diamine (1.5 g, 7.0 mmol, 1.0 equiv) in THF (10 mL) was added CDI portionwise until starting material was consumed as judged by TLC (50% EtOAC/Hexanes; UV). Approximately 10 equiv of carbonyldiimidazole were required. The resulting reaction mixture was cooled to room temperature, and the excess carbonyldiimidazole was quenched by the careful addition of water. The mixture was diluted with EtOAc, and the layers were separated. The organic layer was washed with satd. aq. NaHCO3 twice, and brine once. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Purification by silica gel MPLC provided 6-chloro-1-(pentan-3-yl)-1H-imidazo[4,5-b]pyridin-2-ol as a white solid (1.2 g, 71%). m/z=240.1 [M+H]+

Aufarbeitung

  1. customwas consumed
  2. customThe resulting reaction mixture
  3. customthe excess carbonyldiimidazole was quenched by the careful addition of water
  4. additionThe mixture was diluted with EtOAc
  5. customthe layers were separated
  6. washThe organic layer was washed with satd
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customPurification by silica gel MPLC

Quellen und Nachweise

ORD-Eintrag
ord-373d3db87d304edc97d935269ad0961e
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07851484B2

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