Water → HCID 71294062, compound

HRID 1747556Notes

Reaction equation

HRID 1747556 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:13][C:14]2[C:23]([NH:24][S:25]([CH2:28][CH2:29][CH3:30])(=[O:27])=[O:26])=[N:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=2)[C:9]([F:12])([F:11])[F:10])=[CH:4][N+:3]=1[O-].O.C(=O)([O-])[O-:34].[K+].[K+]>C(OC(=O)C)(=O)C>[F:10][C:9]([F:12])([F:11])[CH:8]([C:5]1[CH:4]=[N:3][C:2]([CH2:1][OH:34])=[CH:7][CH:6]=1)[O:13][C:14]1[C:23]([NH:24][S:25]([CH2:28][CH2:29][CH3:30])(=[O:27])=[O:26])=[N:22][C:21]2[C:16]([N:15]=1)=[CH:17][CH:18]=[CH:19][CH:20]=2

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 67402704HCID 67402704, compound

Product 1

HCID 71294062HCID 71294062, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
100 °C

Procedure

Compound B2 (103 mg, 0.226 mmol) obtained in Step 2 was suspended in acetic anhydride (1.0 mL) and the suspension was stirred at 100° C. for 1.5 hours. Water was added to the reaction mixture. Extraction with ethyl acetate, washing with saturated brine and drying over anhydrous sodium sulfate were performed. The solvent was evaporated under reduced pressure and the resulting residue was dissolved in methanol (2.0 mL). Potassium carbonate (93.7 mg, 0.678 mmol) was added and the mixture was stirred at room temperature for 30 minutes. The solvent was evaporated under reduced pressure, and a saturated aqueous ammonium chloride solution and water were added. Extraction with ethyl acetate, washing with saturated brine and drying over anhydrous sodium sulfate were performed. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1) and further purified by preparative thin-layer chromatography (hexane/ethyl acetate=1/1) to give Compound 31 (30.8 mg, 30% yield).

Workup

  1. extractionExtraction with ethyl acetate
  2. washwashing with saturated brine
  3. dry with materialdrying over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. dissolutionthe resulting residue was dissolved in methanol (2.0 mL)
  6. stirringthe mixture was stirred at room temperature for 30 minutes
  7. customThe solvent was evaporated under reduced pressure
  8. additiona saturated aqueous ammonium chloride solution and water were added
  9. extractionExtraction with ethyl acetate
  10. washwashing with saturated brine
  11. dry with materialdrying over anhydrous sodium sulfate
  12. customThe solvent was evaporated under reduced pressure
  13. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1)
  14. customfurther purified by preparative thin-layer chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-72e2d7b7fb0444e98043a69deb97e312
Source dataset
uspto-grants-2015_10
Patent number
US09150569B2

Reaction notes

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