N-bromobutanimide → HCID 118046029, compound

HRID 595882Notes

Reaction equation

HRID 595882 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5]1[N:6]=[CH:7][C:8]([NH2:11])=[N:9][CH:10]=1.C1C(=O)N([Br:19])C(=O)C1>C(Cl)Cl>[Br:19][C:7]1[C:8]([NH2:11])=[N:9][CH:10]=[C:5]([CH2:4][CH2:3][O:2][CH3:1])[N:6]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 118045473HCID 118045473, compound

Product 1

HCID 118046029HCID 118046029, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(2-methoxyethyl)pyrazin-2-amine (80 mg, 0.522 mmol) in DCM (1.7 mL) was added NBS (93 mg, 0.522 mmol) at room temperature. The reaction mixture was stirred at room temperature for 1 h. After quenched with NaHCO3, the reaction mixture was extracted with DCM 3 times. The combined organic layer was washed with water and brine, dried over anhydrous sodium sulfate. The crude material was used in next step reaction without purification. LCMS (m/z): 232.1/234.1 (MH+), 0.49 min.

Workup

  1. customAfter quenched with NaHCO3
  2. extractionthe reaction mixture was extracted with DCM 3 times
  3. washThe combined organic layer was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe crude material was used in next step reaction without purification
  6. custom232.1/234.1 (MH+), 0.49 min.

Sources & evidence

ORD record
ord-030bdf9a25384bb88821572a32da2ec1
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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