N-bromobutanimide → HCID 118046216, compound

HRID 595885Notes

Reaction equation

HRID 595885 reaction equation
[CH3:1][S:2]([CH2:5][CH2:6][C:7]1[N:8]=[CH:9][C:10]([NH2:13])=[N:11][CH:12]=1)(=[O:4])=[O:3].C1C(=O)N([Br:21])C(=O)C1>C(#N)C>[Br:21][C:9]1[C:10]([NH2:13])=[N:11][CH:12]=[C:7]([CH2:6][CH2:5][S:2]([CH3:1])(=[O:3])=[O:4])[N:8]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 118045746HCID 118045746, compound

Product 1

HCID 118046216HCID 118046216, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 5-(2-(methylsulfonyl)ethyl)pyrazin-2-amine (213 mg, 1.06 mmol) in acetonitrile (6 mL) was added NBS (179 mg, 1.007 mmol) and was stirred at room temperature for 1 h. The solvent was concentrated off to residue. To the crude was added ethyl acetate, washed with saturated sodium carbonate, water (2×), dried sodium sulfate, filtered and concentrated to constant mass to give 210 mg of the desired product as free base used as is, (71% yield). LCMS (m/z): 280.0/282.0 (MH+), 0.38 min.

Workup

  1. concentrationThe solvent was concentrated off to residue
  2. additionTo the crude was added ethyl acetate
  3. washwashed with saturated sodium carbonate, water (2×), dried sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to constant mass

Sources & evidence

ORD record
ord-0e4ec1bd608c4eb398e50364e9419978
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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