N-bromobutanimide → HCID 67363629, compound

HRID 245710Notes

Reaction equation

HRID 245710 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[N:12]3[CH:13]=[CH:14][N:15]=[C:16]([CH3:17])[C:11]3=[CH:10][N:9]=2)[CH2:4][C:3]1=[O:18].[Br:19]N1C(=O)CCC1=O>CN(C)C=O>[Br:19][C:10]1[N:9]=[C:8]([CH:5]2[CH2:6][CH2:7][N:2]([CH3:1])[C:3](=[O:18])[CH2:4]2)[N:12]2[CH:13]=[CH:14][N:15]=[C:16]([CH3:17])[C:11]=12

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 67364160HCID 67364160, compound

Product 1

HCID 67363629HCID 67363629, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-methyl-4-(8-methylimidazo[1,5-a]pyrazin-3-yl)piperidin-2-one (0.205 mmol, 50 mg) in N,N-dimethylformamide (0.6 ml) was added N-bromosuccinimide (0.225 mmol, 40.1 mg) and the reaction mixture was stirred at room temperature for 15 minutes. Extraction dichloromethane/aqueous sodium hydrogen carbonate, drying (sodium sulfate) and concentrating in vacuo yielded the crude product. Purification by column chromatography (silica gel; dichloromethane with 10% methanol) yielded 4-(1-bromo-8-methylimidazo[1,5-a]pyrazin-3-yl)-1-methylpiperidin-2-one (46 mg).

Workup

  1. extractionExtraction dichloromethane/aqueous sodium hydrogen carbonate
  2. dry with materialdrying (sodium sulfate)
  3. concentrationconcentrating in vacuo
  4. customyielded the crude product
  5. customPurification by column chromatography (silica gel; dichloromethane with 10% methanol)

Sources & evidence

ORD record
ord-4fde5e98e20c43d09c1c3745868e6331
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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