HCID 22319110, compound → HCID 22319208, compound

HRID 2356914Notes

Reaction equation

HRID 2356914 reaction equation
C([NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16](=[O:33])[N:17]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:18]=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)[CH:20]=2)=[CH:11][CH:10]=1)(=[O:8])=[O:7])(C)(C)C>FC(F)(F)C(O)=O.C(OCC)(=O)C.O1CCCC1>[S:6]([C:9]1[CH:10]=[CH:11][C:12]([C:15]2[C:16](=[O:33])[N:17]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:18]=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)[CH:20]=2)=[CH:13][CH:14]=1)(=[O:7])(=[O:8])[NH2:5]

Participants

4

Reactant 1

HCID 22319110HCID 22319110, compound

Product 1

HCID 22319208HCID 22319208, compoundYield 85.4%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 21939870Tetrahydrofuran ethyl acetateSolvent

Procedure

80 mg of 3-[4-(tert-butylaminosulfonyl)phenyl]-1-phenyl-5-(2-pyridyl)-1,2-dihydropyridin-2-one was dissolved in 3 ml of trifluoroacetic acid, followed by heating under reflux for 1 hour. It was left to cool to room temperature, and then the reaction mixture was diluted with ethyl acetate/tetrahydrofuran, and washed with a saturated aqueous solution of sodium hydrogen carbonate and brine. The organic layer was dried over magnesium sulfate, and then evaporated. The resulting crude crystals were washed with ethyl acetate, to give 60 mg of the title compound.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 1 hour
  3. waitIt was left
  4. washwashed with a saturated aqueous solution of sodium hydrogen carbonate and brine
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. customevaporated
  7. washThe resulting crude crystals were washed with ethyl acetate

Sources & evidence

ORD record
ord-b050b9493b3f480d86b10cbe1ba12477
Source dataset
uspto-grants-2010_07
Patent number
US07759367B2

Reaction notes

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