N-bromobutanimide → HCID 118054621, compound

HRID 595889Notes

Reaction equation

HRID 595889 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([CH2:8][CH:9]([OH:11])[CH3:10])=[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]([CH2:8][CH:9]([OH:11])[CH3:10])=[N:6][C:7]=1[Br:19]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 118054622HCID 118054622, compound

Product 1

HCID 118054621HCID 118054621, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (+/−)-1-(5-aminopyrazin-2-yl)propan-2-ol (47 mg, 0.307 mmol) in DCM (3.0 mL) was added NBS (49.1 mg, 0.276 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. custom0 (MH+), 0.40 min.

Sources & evidence

ORD record
ord-0a0bbbd8c24d49a79a5976d8bb9fa2b7
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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