N-bromobutanimide → HCID 178473908, compound

HRID 245660Notes

Reaction equation

HRID 245660 reaction equation
[CH3:1][C:2]1[C:3]2[N:4]([C:8]([C@H:11]3[CH2:16][CH2:15][C@H:14]([N:17]4[CH2:22][CH2:21][N:20]([C:23](=[O:25])[CH3:24])[CH2:19][CH2:18]4)[CH2:13][CH2:12]3)=[N:9][CH:10]=2)[CH:5]=[CH:6][N:7]=1.[Br:26]N1C(=O)CCC1=O>CN(C)C=O>[Br:26][C:10]1[N:9]=[C:8]([C@H:11]2[CH2:12][CH2:13][C@H:14]([N:17]3[CH2:18][CH2:19][N:20]([C:23](=[O:25])[CH3:24])[CH2:21][CH2:22]3)[CH2:15][CH2:16]2)[N:4]2[CH:5]=[CH:6][N:7]=[C:2]([CH3:1])[C:3]=12

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 178473909HCID 178473909, compound

Product 1

HCID 178473908HCID 178473908, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 1-(4-((trans)-4-(8-methylimidazo[1,5-a]pyrazin-3-yl)cyclohexyl)piperazin-1-yl)ethanone (0.422 mmol, 144 mg) in N,N-dimethylformamide (2 mL) was added N-bromosuccinimide (0.422 mmol, 75 mg). After two hours at 60° C. the reaction was quenched with a saturated aqueous sodium hydrogencarbonate solution and extracted twice with ethyl acetate. The organic extracts were washed twice with water and brine, dried (sodium sulfate) and concentrated under reduced pressure. The crude product was purified with column chromatography on silica gel (dichloromethane/methanol) to afford 176 mg of the title compound.

Workup

  1. customAfter two hours at 60° C. the reaction was quenched with a saturated aqueous sodium hydrogencarbonate solution
  2. extractionextracted twice with ethyl acetate
  3. washThe organic extracts were washed twice with water and brine
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified with column chromatography on silica gel (dichloromethane/methanol)

Sources & evidence

ORD record
ord-a5e984f399764cbaa0d4b031d62cfd68
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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