N-bromobutanimide → HCID 66651739, compound

HRID 418461Notes

Reaction equation

HRID 418461 reaction equation
Br[N:2]1C(=O)CC[C:3]1=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.C1COCC1>CN1C(=O)CCC1.ClCCl>[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][NH:2][CH3:3])=[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

6

Reactant 3

HCID 67184N-bromobutanimideHCID 10340025HCID 10340025, compoundHCID 66615946Methylamine tetrahydrofuran

Product 1

HCID 66651739HCID 66651739, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

1-Bromo-2,5-pyrrolidinedione (125 mg) was added to a solution of the product from Example 27 step b) (250 mg) in NMP (0.5 ml) and dichloromethane (5 ml), and the solution stirred for 30 min. 2M methylamine/THF (3.25 ml) was then added and the solution stirred for 1 hour. The mixture was diluted with dichloromethane (20 ml), washed with saturated aqueous sodium bicarbonate and water. The organic layer was dried (MgSO4), filtered, 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 (60 mg).

Workup

  1. washwashed with saturated aqueous sodium bicarbonate and water
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customthe residue purified by reverse phase HPLC
  6. customAfter evaporation in vacuo the oily residue
  7. additionwas treated with ether
  8. customto give a solid
  9. filtrationfiltered off
  10. customdried

Sources & evidence

ORD record
ord-878cac43dbe54508b463669983e33ed7
Source dataset
uspto-grants-2012_01
Patent number
US08093278B2

Reaction notes

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