Hydrogen Bromide → HCID 19434901, compound

HRID 1736125Notes

Reaction equation

HRID 1736125 reaction equation
C([N:4]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[O:19][C:20]3[C:28]([F:29])=[CH:27][C:26]([F:30])=[C:25]([NH2:31])[C:21]=3[C:22](=[O:24])[CH:23]=2)=[CH:14][C:13]=1[F:32])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][Br:11])(=O)C.Br.O>O1CCOCC1>[NH2:31][C:25]1[C:21]2[C:22](=[O:24])[CH:23]=[C:18]([C:15]3[CH:16]=[CH:17][C:12]([NH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][Br:11])=[C:13]([F:32])[CH:14]=3)[O:19][C:20]=2[C:28]([F:29])=[CH:27][C:26]=1[F:30]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 962WaterHCID 19434847HCID 19434847, compound

Product 1

HCID 19434901HCID 19434901, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

6.10 g (11.9 mmol) of the resulting 2-[4-[N-acetyl-N-(6-bromohexyl)amino]-3-fluorophenyl]-5-amino-6,8-difluoro-4H-1-benzopyran-4-one was dissolved in 60 ml of dioxane, 40 ml of 47% aqueous HBr was added and the mixture was heated at reflux for 3 hours. The reaction solution was cooled on ice, water was added and the mixture was extracted with ethyl acetate. The organic layer was washed once with 5% aqueous sodium bicarbonate and once with an aqueous saturated solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform:methanol=100:1) to give 3.53 g (63%) of 5-amino-2-[4-(6-bromohexylamino)-3-fluorophenyl]-6,8-difluoro-4H-1-benzopyran-4-one.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 3 hours
  3. additionwas added
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed once with 5% aqueous sodium bicarbonate 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 silica gel column chromatography (chloroform:methanol=100:1)

Sources & evidence

ORD record
ord-c02065b0d4124112a659fecb0282eb3f
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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