Hydrochloric Acid → 2-(4-Carboxymethylamino-3-fluorophenyl)-6,8-difluoro-5-hexylamino-4H-1-benzopyran-4-one

HRID 1736146Notes

Reaction equation

HRID 1736146 reaction equation
C([N:4]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[O:18][C:19]3[C:27]([F:28])=[CH:26][C:25]([F:29])=[C:24]([NH:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[C:20]=3[C:21](=[O:23])[CH:22]=2)=[CH:13][C:12]=1[F:37])[CH2:5][C:6]([O:8]CC)=[O:7])(=O)C.Cl.O>O1CCOCC1>[C:6]([CH2:5][NH:4][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[O:18][C:19]3[C:27]([F:28])=[CH:26][C:25]([F:29])=[C:24]([NH:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[C:20]=3[C:21](=[O:23])[CH:22]=2)=[CH:13][C:12]=1[F:37])([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 194349762-[4-(N-acetyl-N-ethoxycarbonylmethylamino)-3-fluorophenyl]-6,8-difluoro-5-hexylamino-4H-1-benzopyran-4-one

Product 1

HCID 194349852-(4-Carboxymethylamino-3-fluorophenyl)-6,8-difluoro-5-hexylamino-4H-1-benzopyran-4-oneYield 77%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

143 mg (0.276 mmol) of Compound 74 obtained in Example 74 was dissolved in 12 ml of dioxane, 8 ml of concentrated hydrochloric acid was added and the mixture was heated ar reflux for 10 minutes. The reaction solution was cooled on ice, water was added and the mixture was extracted with ethyl acetate. The organic layer was washed twice with water and once with an aqueous saturated solution of sodium chloride and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was recrystallized from ethyl acetate/n-hexane to give 95 mg (77%) of Compound 75.

Workup

  1. temperaturethe mixture was heated ar
  2. temperaturereflux for 10 minutes
  3. additionwas added
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed twice with water and once with an aqueous saturated solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-7012fb3a54b6483a9cdf13bbea0d21c5
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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