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

3-(1-Bromo-8-chloroimidazo[1,5-a]pyrazin-3-yl)cyclobutanone → 3-(1-Bromo-8-chloroimidazo[1,5-A]pyrazin-3-YL)-1-methylcyclobutanol

HRID 1640585
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1640585
[Br:1][C:2]1[N:3]=[C:4]([CH:12]2[CH2:15][C:14](=[O:16])[CH2:13]2)[N:5]2[CH:10]=[CH:9][N:8]=[C:7]([Cl:11])[C:6]=12.[CH3:17][Mg]Cl>C1COCC1>[Br:1][C:2]1[N:3]=[C:4]([CH:12]2[CH2:13][C:14]([CH3:17])([OH:16])[CH2:15]2)[N:5]2[CH:10]=[CH:9][N:8]=[C:7]([Cl:11])[C:6]=12
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 161193273-(1-Bromo-8-chloroimidazo[1,5-a]pyrazin-3-yl)cyclobutanoneHCID 178418332HCID 178418332, Verbindung

Produkt 1

HCID 533286223-(1-Bromo-8-chloroimidazo[1,5-A]pyrazin-3-YL)-1-methylcyclobutanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

3-(1-Bromo-8-chloroimidazo[1,5-a]pyrazin-3-yl)cyclobutanone (51.988 g, 0.17 mol) in anhydrous THF (550 g, 620 mL) under nitrogen at −78° C. was treated with a 3.0 M solution of methyl magnesium chloride in THF (130 mL, 0.38 mol) over 30 min. The mixture was stirred at −78° C. for 30 min and then the cooling bath was removed and the mixture quenched with 14% NH4Cl (132 g). EtOAc was added to the aqueous phase and the pH was adjusted to ˜5 with 20% HCl and the layers separated. The combined organic phases were concentrated in vacuo to a slurry and 0.5 L of toluene was added and the mixture concentrated in vacuo until the EtOAc was removed. The slurry was heated at reflux until homogeneous then allowed to cool to provide desired product, which was isolated by filtration and dried in vacuo. 1H NMR (DMSO-d6, 400 MHz): δ 1.37 (s, 3H), 2.35-2.49 (m, 4H), 3.52 (dddd, 1H, J=9.6, 9.6, 9.6, 9.6 Hz), 5.18 (bs, 1H), 7.37 (d, 1H, J=5.2 Hz) and 8.26 (d, 1H, J=5.2 Hz).

Aufarbeitung

  1. customthe cooling bath was removed
  2. customthe mixture quenched with 14% NH4Cl (132 g)
  3. additionEtOAc was added to the aqueous phase
  4. customthe layers separated
  5. concentrationThe combined organic phases were concentrated in vacuo to a slurry and 0.5 L of toluene
  6. additionwas added
  7. concentrationthe mixture concentrated in vacuo until the EtOAc
  8. customwas removed
  9. temperatureThe slurry was heated
  10. temperatureat reflux until homogeneous
  11. temperatureto cool

Quellen und Nachweise

ORD-Eintrag
ord-bee5365588b940ba9cf184d805408b79
Quelldatensatz
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08114846B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion