N-bromobutanimide → HCID 178476586, compound

HRID 245671Notes

Reaction equation

HRID 245671 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.C(=O)([O-])O.[Na+]>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 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 178476590HCID 178476590, compound

Product 1

HCID 178476586HCID 178476586, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To (trans)-4-(8-methylimidazo[1,5-a]pyrazin-3-yl)cyclohexyl acetate (5.49 mmol, 1.5 g) in N,N-dimethylformamide (15 ml) was added N-bromosuccinimide (5.49 mmol, 0.977 g) and the mixture was stirred at room temperature. After one hour saturated aqueous sodium hydrogencarbonate solution was added and extracted with dichloromethane three times. The combined organic extracts were dried (sodium sulfate) and concentrated in vacuo. The crude product was purified using column chromatography (silica gel; dichloromethane/methanol (gradient 0 to 5% methanol)) to give the title compound (1.8 g).

Workup

  1. extractionextracted with dichloromethane three times
  2. dry with materialThe combined organic extracts were dried (sodium sulfate)
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified

Sources & evidence

ORD record
ord-46bcf6e8e4b44261ab5435fadadf28ae
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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