N-bromobutanimide → HCID 118045699, compound

HRID 595877Notes

Reaction equation

HRID 595877 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[N:6][CH:7]=1.C1C(=O)N([Br:21])C(=O)C1>CC#N>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[N:6][C:7]=1[Br:21]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 118046444HCID 118046444, compound

Product 1

HCID 118045699HCID 118045699, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of methyl 3-(5-aminopyrazin-2-yl)propanoate (25 mg, 0.138 mmol) in CH3CN (690 μL) was added NBS (24.56 mg, 0.138 mmol). The reaction mixture was stirred for 1 h at room temperature. After quenched with Na2S2O3 solution, the reaction mixture was stirred with NaHCO3 solution for 20 min and extracted with EtOAc. The organic layer was washed with water and brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude methyl 3-(5-amino-6-bromopyrazin-2-yl)propanoate was obtained (28%). LCMS (m/z): 260.2/262.2 (MH+), 0.54 min.

Workup

  1. customAfter quenched with Na2S2O3 solution
  2. stirringthe reaction mixture was stirred with NaHCO3 solution for 20 min
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-95ad4d11390c4864b01c897044c5f487
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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