Water → HCID 19434914, compound

HRID 1736151Notes

Reaction equation

HRID 1736151 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][CH3:35])[C:20]=3[C:21](=[O:23])[CH:22]=2)=[CH:13][C:12]=1[F:36])[CH2:5][CH2:6][CH2:7][N:8]=[N+:9]=[N-:10])(=O)C.O>O1CCOCC1.Cl>[N:8]([CH2:7][CH2:6][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][CH3:35])[C:20]=3[C:21](=[O:23])[CH:22]=2)=[CH:13][C:12]=1[F:36])=[N+:9]=[N-:10]

Participants

5

Reactant 2

HCID 962WaterHCID 19434821HCID 19434821, compound

Product 1

HCID 19434914HCID 19434914, compoundYield 56.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

51 mg (0.10 mmol) of the resulting 2-[4-[N-acetyl-N-(3-azidopropyl)amino]-3-fluorophenyl]-6,8-difluoro-5-pentylamino-4H-1-benzopyran-4-one was dissolved in a mixed solvent of 1.5 ml of dioxane and 1.5 ml of concentrated hydrochloric acid and the mixture was heated at reflux for 3 hours. The reaction solution was cooled, water was added, the solution was made weak alkaline and the mixture was extracted twice with ethyl acetate. The organic layer was washed once 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 purified by preparative thin layer chromatography (chloroform) to give 26 mg (56%) of 2-[4-(3-azidopropylamino)-3-fluorophenyl]-6,8-difluoro-5-pentylamino-4H-1-benzopyran-4-one.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 3 hours
  3. temperatureThe reaction solution was cooled
  4. extractionthe mixture was extracted twice with ethyl acetate
  5. washThe organic layer was washed once 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 purified by preparative thin layer chromatography (chloroform)

Sources & evidence

ORD record
ord-b1583d5937ed499693e576725b44d683
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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