Hydrochloric Acid → HCID 19434854, compound

HRID 1736166Notes

Reaction equation

HRID 1736166 reaction equation
[F:1][C:2]1[C:3]([N:35]2[CH2:40][CH2:39][N:38]([CH3:41])[CH2:37][CH2:36]2)=[C:4]([F:34])[C:5]2[O:10][C:9]([C:11]3[CH:16]=[CH:15][C:14]([NH:17]C(=O)C(C)(C)C)=[C:13]([F:24])[CH:12]=3)=[CH:8][C:7](=[O:25])[C:6]=2[C:26]=1[NH:27]C(=O)C(C)(C)C.Cl>O1CCOCC1>[NH2:27][C:26]1[C:6]2[C:7](=[O:25])[CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([NH2:17])=[C:13]([F:24])[CH:12]=3)[O:10][C:5]=2[C:4]([F:34])=[C:3]([N:35]2[CH2:36][CH2:37][N:38]([CH3:41])[CH2:39][CH2:40]2)[C:2]=1[F:1]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19435012HCID 19435012, compound

Product 1

HCID 19434854HCID 19434854, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

340 mg (0.594 mmol) of the above 6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-7-(4-methylpiperazin-1-yl)-5-pivaloylamino-4H-1-benzopyran-4-one was dissolved in 20 mL of 1,4-dioxane, 10 mL of concentrated hydrochloric acid was added and the mixture was heated at reflux for 2.5 hours. The reaction solution was cooled on ice, adjusted to pH 10 and extracted twice with chloroform (containing a small amount of methanol). The organic layer was washed 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=12:1) to give 117 mg of Compound 98 (yield: 49%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 2.5 hours
  3. temperatureThe reaction solution was cooled on ice
  4. extractionextracted twice with chloroform (
  5. additioncontaining a small amount of methanol)
  6. washThe organic layer was washed once with an aqueous saturated solution of sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (chloroform:methanol=12:1)

Sources & evidence

ORD record
ord-d9ac49026cf24b179bd251d526af2dab
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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