N-bromobutanimide → HCID 10069607, compound

HRID 418458Notes

Reaction equation

HRID 418458 reaction equation
BrN1C(=[O:7])CCC1=O.[Cl:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[N:15]([CH2:19][C:20]([OH:22])=[O:21])[C:14]([CH3:23])=[C:13]2[C:24]1[C:33]2[C:28](=[CH:29][C:30]([Cl:34])=[CH:31][CH:32]=2)[N:27]=[CH:26][CH:25]=1>CN(C=O)C.O>[Cl:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[N:15]([CH2:19][C:20]([OH:22])=[O:21])[C:14]([CH2:23][OH:7])=[C:13]2[C:24]1[C:33]2[C:28](=[CH:29][C:30]([Cl:34])=[CH:31][CH:32]=2)[N:27]=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 10340025HCID 10340025, compound

Product 1

HCID 10069607HCID 10069607, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

1-Bromo-2,5-pyrrolidinedione (0.26 g) was added to a solution of the product from Example 27 step b) (0.5 g) in DMF (5 ml) and the solution stirred at room temperature for 20 mins. Water (5 ml) was added and the mixture stirred for a further 30 mins. The reaction was diluted with further water (50 ml), extracted with ethyl acetate, dried (MgSO4) and filtered. The filtrate was evaporated in vacuo and the residue purified by reverse phase HPLC. After evaporation in vacuo the oily residue was treated with ether to give a solid Filtered off and dried to yield the title compound as a white solid (48 mg).

Workup

  1. stirringthe mixture stirred for a further 30 mins
  2. extractionextracted with ethyl acetate
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customThe filtrate was evaporated in vacuo
  6. customthe residue purified by reverse phase HPLC
  7. customAfter evaporation in vacuo the oily residue
  8. additionwas treated with ether
  9. customto give a solid
  10. filtrationFiltered off
  11. customdried

Sources & evidence

ORD record
ord-2fa7d73e766044ca8932d360479909b7
Source dataset
uspto-grants-2012_01
Patent number
US08093278B2

Reaction notes

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