N-bromobutanimide → HCID 66651802, compound

HRID 418463Notes

Reaction equation

HRID 418463 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].[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])=[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 4378561Sodium methanethiolateHCID 10340025HCID 10340025, compound

Product 1

HCID 66651802HCID 66651802, 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 (2 ml), and the solution stirred for 10 min. Sodium thiomethoxide (43 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. The residue was triturated with ether to give a solid, which was filtered and dried to yield the title compound as a white solid (40 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. customThe residue was triturated with ether
  5. customto give a solid, which
  6. filtrationwas filtered
  7. customdried

Sources & evidence

ORD record
ord-22677f65fc5c454f85a6b4758750c946
Source dataset
uspto-grants-2012_01
Patent number
US08093278B2

Reaction notes

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