HCID 67219667, compound → HCID 67219162, compound

HRID 1984720Notes

Reaction equation

HRID 1984720 reaction equation
C([O:4][CH2:5][C:6]([NH:8][CH:9]([C:31]1[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=1)[S:10][C:11]1[C:16]([C:17]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][C:27]([F:30])([F:29])[F:28])=[CH:22][CH:21]=2)=[O:18])=[CH:15][CH:14]=[CH:13][N:12]=1)=[O:7])(=O)C>CO.O1CCCC1.[OH-].[Na+].C(OCC)(=O)C>[OH:4][CH2:5][C:6]([NH:8][CH:9]([C:31]1[CH:32]=[CH:33][N:34]=[CH:35][CH:36]=1)[S:10][C:11]1[C:16]([C:17]([NH:19][C:20]2[CH:21]=[CH:22][C:23]([O:26][C:27]([F:28])([F:29])[F:30])=[CH:24][CH:25]=2)=[O:18])=[CH:15][CH:14]=[CH:13][N:12]=1)=[O:7]

Participants

6

Reactant 1

HCID 67219667HCID 67219667, compound

Product 1

HCID 67219162HCID 67219162, compoundYield 100.2%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

2-(2-Acetoxyacetylaminopyridin-4-ylmethylthio)-N-(4-trifluoromethoxyphenyl)pyridine-3-carboxamide (Compound No. 10-2, 25 mg, 0.048 mmol) was dissolved in the mixture of methanol (2.0 mL) and tetrahydrofuran (1.0 mL), and 4 N aqueous sodium hydroxide solution (60 μL) was added thereto under ice-cooling. The mixture was stirred for 15 minutes at room temperature and diluted with ethyl acetate (30 mL), and then the whole was washed with saturated aqueous sodium hydrogen carbonate solution (30 mL) and brine (30 mL). The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give 23 mg of the target compound quantitatively as a pale yellow solid.

Workup

  1. additionwas added
  2. temperatureunder ice-cooling
  3. washthe whole was washed with saturated aqueous sodium hydrogen carbonate solution (30 mL) and brine (30 mL)
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7081c2c1d9bb43a6abc948dadd2bb2ec
Source dataset
uspto-grants-2009_06
Patent number
US07544703B2

Reaction notes

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