Acetic Acid → (5R)-5-{2-(4-chlorophenyl)-2-[6-methoxy-5-(1H-pyrazol-4-yl)pyridin-2-yl]ethyl}pyrrolidin-2-one

HRID 70693Notes

Reaction equation

HRID 70693 reaction equation
C(O)(=O)C.[Cl:5][C:6]1[CH:11]=[CH:10][C:9](/[C:12](/[C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:27]=[N:28][NH:29][CH:30]=3)=[C:22]([O:31][CH3:32])[N:21]=2)=[CH:13]\[C@@H:14]2[NH:18][C:17](=[O:19])[CH2:16][CH2:15]2)=[CH:8][CH:7]=1.[H][H]>CO.[Pd]>[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:30]=[N:29][NH:28][CH:27]=3)=[C:22]([O:31][CH3:32])[N:21]=2)[CH2:13][C@@H:14]2[NH:18][C:17](=[O:19])[CH2:16][CH2:15]2)=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 67396156HCID 67396156, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67397423(5R)-5-{2-(4-chlorophenyl)-2-[6-methoxy-5-(1H-pyrazol-4-yl)pyridin-2-yl]ethyl}pyrrolidin-2-oneYield 62.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% palladium-activated carbon (60 mg) and acetic acid (2 mL) were added to a solution of (5R)-5-{(E)-2-(4-chlorophenyl)-2-[6-methoxy-5-(1H-pyrazol-4-yl)pyridin-2-yl]ethenyl}pyrrolidin-2-one (122 mg) in methanol (3 mL) in a hydrogen gas stream, and the mixture was stirred at room temperature for 20 hours. The reaction solution was filtered through celite, and then the solvent was evaporated under reduced pressure. Saturated aqueous sodium bicarbonate was added to the residue, followed by extraction with chloroform. The solvent was evaporated from the organic layer under reduced pressure to give a crude product of (5R)-5-{2-(4-chlorophenyl)-2-[6-methoxy-5-(1H-pyrazol-4-yl)pyridin-2-yl]ethyl}pyrrolidin-2-one as a yellow oil (77 mg).

Workup

  1. filtrationThe reaction solution was filtered through celite
  2. customthe solvent was evaporated under reduced pressure
  3. additionSaturated aqueous sodium bicarbonate was added to the residue
  4. extractionfollowed by extraction with chloroform
  5. customThe solvent was evaporated from the organic layer under reduced pressure

Sources & evidence

ORD record
ord-cfdfa32d4e394908bc221ba32f40defc
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

Loading…