Trifluoroacetic acid → 4-[(5-Chloro-2-pyridinyl)methoxy]-1-(4-{[(3R)-3-pyrrolidinyl]oxy}phenyl)-1H-pyridin-2-one

HRID 15080Notes

Reaction equation

HRID 15080 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][O:16][C:17]2[CH:22]=[CH:21][N:20]([C:23]3[CH:28]=[CH:27][C:26]([O:29][C@@H:30]4[CH2:34][CH2:33][N:32](C(OC(C)(C)C)=O)[CH2:31]4)=[CH:25][CH:24]=3)[C:19](=[O:42])[CH:18]=2)=[N:13][CH:14]=1>C(Cl)(Cl)Cl>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][O:16][C:17]2[CH:22]=[CH:21][N:20]([C:23]3[CH:24]=[CH:25][C:26]([O:29][C@@H:30]4[CH2:34][CH2:33][NH:32][CH2:31]4)=[CH:27][CH:28]=3)[C:19](=[O:42])[CH:18]=2)=[N:13][CH:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 589649934-[(5-chloro-2-pyridinyl)methoxy]-1-(4-{[(3R)-1-(tert-butoxycarbonyl)-3-pyrrolidinyl]oxy}phenyl)-1H-pyridin-2-one

Product 1

HCID 589648824-[(5-Chloro-2-pyridinyl)methoxy]-1-(4-{[(3R)-3-pyrrolidinyl]oxy}phenyl)-1H-pyridin-2-oneYield 105.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Trifluoroacetic acid (20 mL) was added to chloroform solution (20 mL) of 4-[(5-chloro-2-pyridinyl)methoxy]-1-(4-{[(3R)-1-(tert-butoxycarbonyl)-3-pyrrolidinyl]oxy}phenyl)-1H-pyridin-2-one (3.14 g, Example 121), and stirred at room temperature for an hour. After concentrating the reaction liquid, 1N sodium hydroxide solution was added thereto, followed by extraction with chloroform two times. The organic layer was washed with saturated brine, dried over anhydrous potassium carbonate, and the solvent was concentrated under reduced pressure to provide the title compound (2.65 g, 83%).

Workup

  1. concentrationAfter concentrating
  2. customthe reaction liquid, 1N sodium hydroxide solution
  3. additionwas added
  4. extractionfollowed by extraction with chloroform two times
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous potassium carbonate
  7. concentrationthe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-27c4e513a57c4114abce409aa9358836
Source dataset
uspto-grants-2010_06
Patent number
US07732456B2

Reaction notes

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