Water → HCID 178476585, Verbindung

HRID 245767Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 245767
[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@@H:8]([C:11]2[N:15]3[CH:16]=[CH:17][N:18]=[C:19]([CH3:20])[C:14]3=[CH:13][N:12]=2)[CH2:7][CH2:6]1)(=[O:3])[CH3:2].[Br:21]N1C(=O)CCC1=O.O>CN(C)C=O>[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@@H:8]([C:11]2[N:15]3[CH:16]=[CH:17][N:18]=[C:19]([CH3:20])[C:14]3=[C:13]([Br:21])[N:12]=2)[CH2:7][CH2:6]1)(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 178476589HCID 178476589, Verbindung

Produkt 1

HCID 178476585HCID 178476585, VerbindungAusbeute 93,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To (cis)-4-(8-methylimidazo[1,5-a]pyrazin-3-yl)cyclohexyl acetate (46.8 mmol, 12.8 g) in N,N-dimethylformamide (100 ml) was added N-bromosuccinimide (46.8 mmol, 8.33 g). After stirring at room temperature for one hour the reaction mixture was poured into water and extracted with dichloromethane twice. The combined organic layers were washed with water twice, washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography (silica gel; dichloromethane with gradient 0 to 3% of methanol) to give (cis)-4-(1-bromo-8-methylimidazo[1,5-a]pyrazin-3-yl)cyclohexyl acetate (15.34 g).

Aufarbeitung

  1. extractionextracted with dichloromethane twice
  2. washThe combined organic layers were washed with water twice
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (silica gel; dichloromethane with gradient 0 to 3% of methanol)

Quellen und Nachweise

ORD-Eintrag
ord-baf218129b37482db90a5b1057f8da22
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658794B2

Notizen zur Reaktion

Wird geladen…