N-bromobutanimide → HCID 118045762, compound

HRID 595899Notes

Reaction equation

HRID 595899 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]#[N:11])=[N:6][CH:7]=1.C1C(=O)N([Br:19])C(=O)C1>C(Cl)Cl>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]#[N:11])=[N:6][C:7]=1[Br:19]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 118045591HCID 118045591, compound

Product 1

HCID 118045762HCID 118045762, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-(5-aminopyrazin-2-yl)propanenitrile (45 mg, 0.304 mmol) in DCM (1519 μL) was added NBS (48.7 mg, 0.273 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 10 min. After quenched with 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): 227/229.1 (MH+), 0.45 min.

Workup

  1. customAfter quenched with 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. custom227/229.1 (MH+), 0.45 min.

Sources & evidence

ORD record
ord-12cdc577859f4b56b447a416a624ffa5
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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