N-bromobutanimide → HCID 118045272, compound

HRID 595894Notes

Reaction equation

HRID 595894 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][C:6]1[N:7]=[CH:8][C:9]([NH2:12])=[N:10][CH:11]=1)[CH3:2].C1C(=O)N([Br:20])C(=O)C1>C(Cl)Cl>[Br:20][C:8]1[C:9]([NH2:12])=[N:10][CH:11]=[C:6]([CH2:5][CH2:4][O:3][CH2:1][CH3:2])[N:7]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 118046020HCID 118046020, compound

Product 1

HCID 118045272HCID 118045272, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-(2-ethoxyethyl)pyrazin-2-amine (45 mg, 0.269 mmol) in DCM (897 μL) was added NBS (43.1 mg, 0.242 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 10 min. After quenched with sat. NaHCO3, the reaction mixture was extracted with EtOAc 3 times. The combined organic layer was washed with water and brine, dried over anhydrous sodium sulfate. Filtered and concentrated in vacuo. The crude product was used in next step reaction without purification. LCMS (m/z): 246.0 (MH+), 0.59 min.

Workup

  1. customAfter quenched with sat. NaHCO3
  2. extractionthe reaction mixture was extracted with EtOAc 3 times
  3. washThe combined organic layer was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationFiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was used in next step reaction without purification
  8. custom246.0 (MH+), 0.59 min.

Sources & evidence

ORD record
ord-d2020c1c6a4144579da14e05979eca35
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

Loading…