Dimethyl Sulfoxide → HCID 21090459, Verbindung

HRID 350852

Reaktionsgleichung

Reaktionsgleichung von HRID 350852
CS(C)=O.[CH3:5][C:6]([O:9][C:10]([NH:12][CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)=[O:11])([CH3:8])[CH3:7].[F:19][C:20]1[CH:27]=[C:26](F)[CH:25]=[C:24]([F:29])[C:21]=1[C:22]#[N:23].C(=O)([O-])[O-].[K+].[K+]>O>[C:22]([C:21]1[C:20]([F:19])=[CH:27][C:26]([N:16]2[CH2:15][CH2:14][CH:13]([NH:12][C:10](=[O:11])[O:9][C:6]([CH3:5])([CH3:7])[CH3:8])[CH2:18][CH2:17]2)=[CH:25][C:24]=1[F:29])#[N:23]

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 7238334-(N-Boc-amino)piperidineHCID 7371772,4,6-Trifluorobenzonitrile

Produkt 1

HCID 21090459HCID 21090459, VerbindungAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A DMSO (25 mL, 0.1M) solution containing 4-N—BOC-aminopiperidine (500 mg, 2.5 mmol, 1.0 eq), 2,4,6-trifluorobenzonitrile (393 mg, 2.5 mmol, 1.0 eq), and potassium carbonate (691 mg, 5.0 mmol, 2.0 eq) was heated to 100° C. for 18 h. The resulting mixture was cooled to RT, poured in H2O (ca 50 mL), and extracted (3×) with EtOAc. The combined extracts were washed (2×) with H2O, dried over MgSO4, and concentrated in vacuo. The resulting solid was purified via flash chromatography using 1:1 hexanes/EtOAc as the mobile phase. Isolated 594 mg (1.76 mmol, 70% yield).

Aufarbeitung

  1. temperatureThe resulting mixture was cooled to RT
  2. extractionextracted (3×) with EtOAc
  3. washThe combined extracts were washed (2×) with H2O
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe resulting solid was purified via flash chromatography
  7. customIsolated 594 mg (1.76 mmol, 70% yield)

Quellen und Nachweise

ORD-Eintrag
ord-0e0c075c869b467b95382bbad83c4d99
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07183290B2

Verknüpfte Notizen

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