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

HRID 70694Notes

Reaction equation

HRID 70694 reaction equation
Cl.[CH:2]1([S:5]([C:8]2[CH:13]=[CH:12][C:11](/[C:14](/[C:22]3[CH:27]=[CH:26][C:25]([C:28]4[CH:29]=[N:30][NH:31][CH:32]=4)=[C:24]([O:33][CH3:34])[N:23]=3)=[CH:15]\[C@@H:16]3[NH:20][C:19](=[O:21])[CH2:18][CH2:17]3)=[CH:10][CH:9]=2)(=[O:7])=[O:6])[CH2:4][CH2:3]1.[H][H]>CO.[Pd]>[CH:2]1([S:5]([C:8]2[CH:9]=[CH:10][C:11]([CH:14]([C:22]3[CH:27]=[CH:26][C:25]([C:28]4[CH:29]=[N:30][NH:31][CH:32]=4)=[C:24]([O:33][CH3:34])[N:23]=3)[CH2:15][C@@H:16]3[NH:20][C:19](=[O:21])[CH2:18][CH2:17]3)=[CH:12][CH:13]=2)(=[O:6])=[O:7])[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 67397195HCID 67397195, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67400754(5R)-5-{2-[4-(cyclopropylsulfonyl)phenyl]-2-[6-methoxy-5-(1H-pyrazol-4-yl)pyridin-2-yl]ethyl}pyrrolidin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% palladium-activated carbon (175 mg) and concentrated hydrochloric acid (1 mL) were added to a solution of (5R)-5-{(E)-2-[4-(cyclopropylsulfonyl)phenyl]-2-[6-methoxy-5-(1H-pyrazol-4-yl)pyridin-2-yl]ethenyl}pyrrolidin-2-one obtained in Example 4-376(1) (175 mg) in methanol (3 mL) in a hydrogen gas stream, and the mixture was stirred at room temperature for five 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-(cyclopropylsulfonyl)phenyl]-2-[6-methoxy-5-(1H-pyrazol-4-yl)pyridin-2-yl]ethyl}pyrrolidin-2-one as a colorless amorphous (129 mg, 73%).

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-90343137b00742e0a4ac3ebcaf3ee417
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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