N-bromobutanimide → HCID 10364503, compound

HRID 418459Notes

Reaction equation

HRID 418459 reaction equation
BrN1[C:6](=[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.CO>[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][O:7][CH3:6])=[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 10364503HCID 10364503, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 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 methanol (2 ml), and the solution stirred for 1 h. The solvents were 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 which was filtered and dried to yield the title compound as a white solid (48 mg).

Workup

  1. customThe solvents were evaporated in vacuo
  2. customthe residue purified by reverse phase HPLC
  3. customAfter evaporation in vacuo the oily residue
  4. additionwas treated with ether
  5. customto give a solid which
  6. filtrationwas filtered
  7. customdried

Sources & evidence

ORD record
ord-34c5dde44d8e4022bdff428607289369
Source dataset
uspto-grants-2012_01
Patent number
US08093278B2

Reaction notes

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