N-bromobutanimide → HCID 178432910, compound

HRID 245742Notes

Reaction equation

HRID 245742 reaction equation
[CH2:1]([O:8][C:9](=[O:28])[NH:10][CH2:11][C@H:12]1[CH2:17][CH2:16][C@H:15]([C:18]2[N:22]3[CH:23]=[CH:24][N:25]=[C:26]([CH3:27])[C:21]3=[CH:20][N:19]=2)[CH2:14][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:29]N1C(=O)CCC1=O>CN(C)C=O>[Br:29][C:20]1[N:19]=[C:18]([C@H:15]2[CH2:16][CH2:17][C@H:12]([CH2:11][NH:10][C:9](=[O:28])[O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:13][CH2:14]2)[N:22]2[CH:23]=[CH:24][N:25]=[C:26]([CH3:27])[C:21]=12

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 178432918HCID 178432918, compound

Product 1

HCID 178432910HCID 178432910, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To benzyl((trans)-4-(8-methylimidazo[1,5-a]pyrazin-3-yl)cyclohexyl)methylcarbamate (3.52 g, 9.05 mmol) in N,N-dimethylformamide (35 ml) was added N-bromosuccinimide (1.611 g, 9.05 mmol) and the mixture was stirred at room temperature for four hours. The reaction was quenched with saturated aqueous sodium hydrogencarbonate and subsequently extracted three times with dichloromethane. The combined organic layers were washed with brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by column chromatography (silica gel, dichloromethane with gradient 0 to 5% of methanol) to yield benzyl ((trans)-4-(1-bromo-8-methylimidazo[1,5-a]pyrazin-3-yl)cyclohexyl)methylcarbamate (3.01 g).

Workup

  1. customThe reaction was quenched with saturated aqueous sodium hydrogencarbonate
  2. extractionsubsequently extracted three times with dichloromethane
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (silica gel, dichloromethane with gradient 0 to 5% of methanol)

Sources & evidence

ORD record
ord-b60ae13cfd324b4aa8ce866561d29274
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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