Acetic Anhydride → HCID 18447366, compound

HRID 1269849Notes

Reaction equation

HRID 1269849 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][C:18]3[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=3[NH2:20])=[CH:14][CH:15]=2)[CH:10]=[N:9]1.C(=O)([O-])O.[Na+]>N1C=CC=CC=1>[NH:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][C:18]3[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=3[NH:20][C:1](=[O:3])[CH3:2])=[CH:14][CH:15]=2)[CH:10]=[N:9]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 22934031HCID 22934031, compound

Product 1

HCID 18447366HCID 18447366, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetic anhydride (0.04 ml) was added to a solution of the 2-(1H-indazol-5-yloxy)aniline (34 mg, 0.151 mmol) obtained in Example 476 in pyridine (1 ml) at room temperature, and the resulting mixture was stirred at room temperature for 2 hours. The reaction solution was cooled to 0° C. and a saturated aqueous sodium hydrogencarbonate solution was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was dissolved in a mixed solution of tetrahydrofuran (1 ml) and methanol (1 ml), followed by adding thereto 1N aqueous sodium hydroxide solution (1 ml). The resulting mixture was stirred at room temperature for 1 hour. The reaction solution was added to a saturated aqueous sodium chloride solution and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent, and the resulting residue was purified by a silica gel column chromatography (chloroform/methanol) to obtain N-[2-(1H-indazol-5-yloxy)phenyl]acetamide (32 mg, 79%).

Workup

  1. temperatureThe reaction solution was cooled to 0° C.
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. dissolutionthe resulting residue was dissolved in a mixed solution of tetrahydrofuran (1 ml) and methanol (1 ml)
  7. additionby adding
  8. stirringThe resulting mixture was stirred at room temperature for 1 hour
  9. additionThe reaction solution was added to a saturated aqueous sodium chloride solution
  10. extractionextracted with chloroform
  11. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  12. distillationdistilled under reduced pressure
  13. customto remove the solvent
  14. customthe resulting residue was purified by a silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-055516249cf444089ddd9981973c24c3
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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