N-bromobutanimide → HCID 118054582, compound

HRID 595897Notes

Reaction equation

HRID 595897 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([CH:8]([CH3:11])[CH2:9][OH:10])=[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]([CH:8]([CH3:11])[CH2:9][OH:10])=[N:6][C:7]=1[Br:19]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 118046398HCID 118046398, compound

Product 1

HCID 118054582HCID 118054582, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(5-aminopyrazin-2-yl)propan-1-ol (30 mg, 0.196 mmol) in DCM (653 μL) was added NBS (31.4 mg, 0.176 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): 234.0 (MH+), 0.40 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. custom234.0 (MH+), 0.40 min.

Sources & evidence

ORD record
ord-4dffb36a32d44604b6792e4a346f710c
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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