Hydrochloric Acid → HCID 18008893, compound

HRID 987481Notes

Reaction equation

HRID 987481 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[CH:16]=[CH:15][C:14]([CH:17]=O)=[CH:13]1)[N:8]=[C:7]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:6](=[O:24])[NH:5]2.Cl.[NH2:26]O.C([O-])(=O)C.[Na+].Cl>C(O)C.[Pd].ClCCl.C(O)C>[ClH:1].[NH2:26][CH2:17][C:14]1[CH:15]=[CH:16][N:12]([C:11]2[CH:10]=[C:9]3[C:4]([NH:5][C:6](=[O:24])[CH:7]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[NH:8]3)=[CH:3][C:2]=2[Cl:1])[CH:13]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 9906201HCID 9906201, compound

Product 1

HCID 18008893HCID 18008893, compoundYield 66.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×HCID 21584144Dichloromethane ethanolSolvent

Procedure

To a solution of the compound of Example 1 (166 mg, 480 μmol) in ethanol (5 ml) were added hydroxylamine hydrochloride (66.7 mg, 960 μmol) and successively sodium acetate (78.7 mg, 960 μmol), and the mixture was refluxed for 3 hours. After cooling, the insolubles were filtered off and solvent was distilled off. The residue obtained was submitted to silica gel column chromatography [dichloromethane-ethanol=10:1] to obtain yellowish brown powder. After dissolved this into ethanol (10 ml), 10% palladium on carbon (containing 51.1% moisture, 50.0 mg) and successively concentrated hydrochloric acid (0.5 ml) were added and the mixture was stirred for 2 hours at room temperature under hydrogen atmosphere (4 Kgf/cm2) (392 KPa). Catalyst was filtered off using celite and solvent was distilled off. Acetone was added to the residue obtained and the crystals were collected by filtration. After washed with acetone, these were air-dried, thereby obtaining 61.2 mg of title compound as colorless powder. Yield 33%.

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. temperatureAfter cooling
  3. filtrationthe insolubles were filtered off
  4. distillationsolvent was distilled off
  5. customThe residue obtained
  6. customto obtain yellowish brown powder
  7. additionwere added
  8. filtrationCatalyst was filtered off
  9. distillationwas distilled off
  10. additionAcetone was added to the residue
  11. customobtained
  12. filtrationthe crystals were collected by filtration
  13. washAfter washed with acetone
  14. customthese were air-dried

Sources & evidence

ORD record
ord-ca993c5308f54c11aeac0a57b8a9df8d
Source dataset
uspto-grants-2003_10
Patent number
US06632813B1

Reaction notes

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