Triethylamine → HCID 76849200, Verbindung

HRID 921716Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 921716
[C:1]([C:4]1[N:9]=[C:8]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:7]=[CH:6][CH:5]=1)(=O)[NH2:2].C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>ClCCl>[C:1]([C:4]1[N:9]=[C:8]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:15])([CH3:14])[CH3:16])[CH:7]=[CH:6][CH:5]=1)#[N:2]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 86708592HCID 86708592, Verbindung

Produkt 1

HCID 76849200HCID 76849200, VerbindungAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a round bottom flask charged with tert-butyl (6-carbamoylpyridin-2-yl)carbamate (0.940 g, 3.96 mmol) in dichloromethane (7.92 ml) was added triethylamine (1.380 ml, 9.90 mmol). The reaction mixture was cooled to 0° C. and trifluoroacetic anhydride (0.671 ml, 4.75 mmol) was added dropwise. The reaction mixture was stirred at 0° C. 90 min. The reaction mixture was quenched with saturated aqueous sodium bicarbonate and transferred to a separatory funnel. The aqueous layer was extracted with dichloromethane (2×). The combined organics were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude residue was purified by column chromatography on the ISCO system (40 g, 0-15% EtOAc/Hex) to provide tert-butyl (6-cyanopyridin-2-yl)carbamate (0.538 g).

Aufarbeitung

  1. custom90 min
  2. customThe reaction mixture was quenched with saturated aqueous sodium bicarbonate
  3. customtransferred to a separatory funnel
  4. extractionThe aqueous layer was extracted with dichloromethane (2×)
  5. washThe combined organics were washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude residue was purified by column chromatography on the ISCO system (40 g, 0-15% EtOAc/Hex)

Quellen und Nachweise

ORD-Eintrag
ord-911cc26d13824ffa9a6b88ce2e5285c4
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09273057B2

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