StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Potassium Carbonate → (4S,6S)-4-(5-(6-ethynylpyridin-3-yl)-2-fluorophenyl)-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine

HRID 930326
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 930326
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][C:11]([C:14]#[C:15][Si](C)(C)C)=[CH:12][CH:13]=2)=[CH:4][C:3]=1[C@:20]1([CH2:31][F:32])[CH2:25][C@@H:24]([C:26]([F:29])([F:28])[F:27])[O:23][C:22]([NH2:30])=[N:21]1.C(=O)([O-])[O-].[K+].[K+]>CO>[C:14]([C:11]1[N:10]=[CH:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[C:3]([C@:20]3([CH2:31][F:32])[CH2:25][C@@H:24]([C:26]([F:27])([F:28])[F:29])[O:23][C:22]([NH2:30])=[N:21]3)[CH:4]=2)=[CH:13][CH:12]=1)#[CH:15]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 11430Potassium CarbonateHCID 86732153(4S,6S)-4-(2-fluoro-5-(6-((trimethylsilyl)ethynyl)pyridin-3-yl)phenyl)-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine

Produkt 1

HCID 86732154(4S,6S)-4-(5-(6-ethynylpyridin-3-yl)-2-fluorophenyl)-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amineAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887
Methanol
Lösungsmittel

Versuchsvorschrift

A mixture of (4S,6S)-4-(2-fluoro-5-(6-((trimethylsilyl)ethynyl)pyridin-3-yl)phenyl)-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine (0.2034 g, 0.435 mmol, Example 111), potassium carbonate (0.301 g, 2.175 mmol), and MeOH (3 mL) was stirred at room temperature for 1.25 h. The reaction mixture was concentrated in vacuo, diluted with water and extracted with DCM three times. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated. The crude material was purified by silica gel chromatography: 0-100% EtOAc/hexane in 12 min. The product was obtained as a white solid (0.16 g, 93% yield). MS m/z=396 [M+H]+. Calculated for C19H14F5N3O: 395.3.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with water
  3. extractionextracted with DCM three times
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude material was purified by silica gel chromatography
  9. wait0-100% EtOAc/hexane in 12 min

Quellen und Nachweise

ORD-Eintrag
ord-aeb9a3ceb3f04a11a6a107089c85618c
Quelldatensatz
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09296734B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion