Pyrrolidine → HCID 11753793, compound

HRID 418462Notes

Reaction equation

HRID 418462 reaction equation
Br[N:2]1[C:6](=O)[CH2:5][CH2:4][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.N1CCCC1>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][N:2]1[CH2:6][CH2:5][CH2:4][CH2:3]1)=[C:13]2[C:24]1[C:33]2[CH2:32][CH:31]=[C:30]([Cl:34])[CH2:29][C:28]=2[N:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 67184N-bromobutanimideHCID 10340025HCID 10340025, compound

Product 1

HCID 11753793HCID 11753793, compoundYield 19.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Bromo-2,5-pyrrolidinedione (165 mg) was added to a solution of the product from Example 27 (0.3 g) in DMF (3 ml), and the solution stirred for 10 min. Pyrrolidine (0.5 ml) was then added and the mixture stirred for a further 30 min. 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 off and dried to yield the title compound as a white solid (70 mg).

Workup

  1. stirringthe mixture stirred for a further 30 min
  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 which
  7. filtrationwas filtered off
  8. customdried

Sources & evidence

ORD record
ord-44c2a03f48b54e2c95549dcd7ff99e40
Source dataset
uspto-grants-2012_01
Patent number
US08093278B2

Reaction notes

Loading…