Pyrrolidine → HCID 22350926, compound

HRID 747529Notes

Reaction equation

HRID 747529 reaction equation
Br[CH2:2][C:3]([NH:5][CH2:6][CH2:7][CH2:8][N:9]1[C:13]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[CH:16][CH:15]=2)=[CH:12][S:11][C:10]1=[N:26][C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=1)=[O:4].[NH:34]1[CH2:38][CH2:37][CH2:36][CH2:35]1.C(=O)([O-])O.[Na+]>CN(C)C=O>[F:33][C:30]1[CH:31]=[CH:32][C:27]([N:26]=[C:10]2[N:9]([CH2:8][CH2:7][CH2:6][NH:5][C:3](=[O:4])[CH2:2][N:34]3[CH2:38][CH2:37][CH2:36][CH2:35]3)[C:13]([C:14]3[CH:19]=[CH:18][C:17]([N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)=[CH:16][CH:15]=3)=[CH:12][S:11]2)=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 516892Sodium BicarbonateHCID 22350983HCID 22350983, compound

Product 1

HCID 22350926HCID 22350926, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the compound (200 mg) obtained in Example 356, pyrrolidine (0.32 ml) and N,N-dimethylformamide (2 ml) was stirred at room temperature for 8 hours. To the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated brine, dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography [chloroform:methanol (97:3)] to give the title compound (123 mg) as oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated brine
  3. dry with materialdried over sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography [chloroform:methanol (97:3)]

Sources & evidence

ORD record
ord-77f37f4c18364bbb89e5d146c25a6470
Source dataset
uspto-grants-2008_07
Patent number
US07396842B2

Reaction notes

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