Water → HCID 178476585, compound

HRID 245767Notes

Reaction equation

HRID 245767 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 178476585HCID 178476585, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-baf218129b37482db90a5b1057f8da22
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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