Acetoxyacetyl chloride → HCID 23150981, compound

HRID 1984721Notes

Reaction equation

HRID 1984721 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH2:8][S:9][C:10]2[C:15]([C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=3)=[O:17])=[CH:14][CH:13]=[CH:12][N:11]=2)[CH:5]=[CH:4][N:3]=1.[C:30]([O:33][CH2:34][C:35](Cl)=[O:36])(=[O:32])[CH3:31]>N1C=CC=CC=1.C(OCC)(=O)C>[C:30]([O:33][CH2:34][C:35]([N:1]([C:35](=[O:36])[CH2:34][O:33][C:30](=[O:32])[CH3:31])[C:2]1[CH:7]=[C:6]([CH2:8][S:9][C:10]2[C:15]([C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][C:26]([F:28])([F:29])[F:27])=[CH:21][CH:20]=3)=[O:17])=[CH:14][CH:13]=[CH:12][N:11]=2)[CH:5]=[CH:4][N:3]=1)=[O:36])(=[O:32])[CH3:31]

Participants

5

Reactant 2

HCID 26297Acetoxyacetyl chlorideHCID 11258671HCID 11258671, compound

Product 1

HCID 23150981HCID 23150981, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(2-Aminopyridin-4-ylmethylthio)-N-(4-trifluoromethoxyphenyl)pyridine-3-carboxamide (Compound No. 3-11, 800 mg, 1.9 mmol) was dissolved in pyridine (10 mL), and acetoxyacetyl chloride (0.66 mL, 6.1 mmol) was added thereto under ice-cooling, and the mixture was stirred for 18 hours at room temperature. The mixture was diluted with ethyl acetate (100 mL), and the whole was washed with saturated aqueous sodium hydrogen carbonate solution (100 mL) and 1 N hydrochloric acid (50 mL) twice successively. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution (100 mL) again and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The resulting solid was recrystallized from ethyl acetate-hexane to give 300 mg of the target compound as a colorless solid. (Yield 30%)

Workup

  1. temperatureunder ice-cooling
  2. washthe whole was washed with saturated aqueous sodium hydrogen carbonate solution (100 mL) and 1 N hydrochloric acid (50 mL) twice successively
  3. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution (100 mL) again
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe resulting solid was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-4ed9048d07be4384a45002e9c963a024
Source dataset
uspto-grants-2009_06
Patent number
US07544703B2

Reaction notes

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