Triethylamine → HCID 22170450, Verbindung

HRID 736392Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 736392
[Cl:1][C:2]1[C:3]([C:8]2[CH:16]=[CH:15][C:11](C(O)=O)=[CH:10][CH:9]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.C([N:19](CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>CN(C=O)C.O>[Cl:1][C:2]1[C:3]([C:8]2[CH:16]=[CH:15][C:11]([NH2:19])=[CH:10][CH:9]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 221704544-(3-Chloropyridin-2-yl)benzoic acid

Produkt 1

HCID 22170450HCID 22170450, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

The product from Example 24A (104 mg, 0.444 mmol) and triethylamine (0.095 mL, 0.68 mmol) were combined in DMF (3 mL) and treated with diphenylphosphoryl azide (0.14 mL, 0.65 mmol). After stirring for 4 hours, the mixture was treated with water (0.30 mL) and heated at 65° C. for 1 hour. The mixture was allowed to cool to room temperature, diluted with water (7 mL), and extracted with diethyl ether (7 mL). The organic layer was washed with brine (7 mL), dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (50% ethyl acetate in hexanes) to provide the title compound.

Aufarbeitung

  1. temperatureto cool to room temperature
  2. extractionextracted with diethyl ether (7 mL)
  3. washThe organic layer was washed with brine (7 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under reduced pressure
  7. customThe residue was purified by flash chromatography (50% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-8e502149ac9b4b9e92e196dca4771364
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07595332B2

Notizen zur Reaktion

Wird geladen…