N-bromobutanimide → HCID 66651945, compound

HRID 418464Notes

Reaction equation

HRID 418464 reaction equation
BrN1C(=O)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.[CH3:35][S:36]([O-:38])=[O:37].[Na+]>CN(C=O)C>[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][S:36]([CH3:35])(=[O:38])=[O:37])=[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 3

HCID 67184N-bromobutanimideHCID 2733271Sodium methanesulfinateHCID 10340025HCID 10340025, compound

Product 1

HCID 66651945HCID 66651945, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Bromo-2,5-pyrrolidinedione (0.11 g) was added to a solution of the product from Example 27 step b) (0.2 g) in DMF (5 ml), and the solution stirred for 10 min. Sodium methanesulfinate (63 mg) was then added and the mixture stirred for a further 3 hours. 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. Filtered off and dried to yield the title compound as a white solid (50 mg).

Workup

  1. stirringthe mixture stirred for a further 3 hours
  2. customThe solvents were evaporated in vacuo
  3. customthe residue purified by reverse phase HPLC
  4. customAfter evaporation in vacuo the oily residue
  5. additionwas treated with ether
  6. customto give a solid
  7. filtrationFiltered off
  8. customdried

Sources & evidence

ORD record
ord-4d17e836feaa46f8823843f26140f776
Source dataset
uspto-grants-2012_01
Patent number
US08093278B2

Reaction notes

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