HCID 178418361, compound → HCID 21250297, compound

HRID 1531744Notes

Reaction equation

HRID 1531744 reaction equation
[C:1]([C:4]1([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[N:13]([CH3:17])[C:12](=[O:18])[C:11]([CH2:19][C:20]2[CH:29]=[CH:28][C:23]([C:24]([NH:26]O)=[NH:25])=[CH:22][CH:21]=2)=[N:10]3)[CH2:6][CH2:5]1)([OH:3])=[O:2].[H][H]>C(O)(=O)C.[Pd]>[C:1]([C:4]1([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[N:13]([CH3:17])[C:12](=[O:18])[C:11]([CH2:19][C:20]2[CH:21]=[CH:22][C:23]([C:24]([NH2:26])=[NH:25])=[CH:28][CH:29]=2)=[N:10]3)[CH2:6][CH2:5]1)([OH:3])=[O:2]

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178481488HCID 178481488, compound

Product 1

HCID 21250297HCID 21250297, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

300 mg (0.76 mmol) of 4-{[6-(1-carboxy-cyclopropyl)-1-methyl-2-oxo-1,2-dihydroquinoxalin-3-yl]-methyl}-N-hydroxybenzamidine are dissolved in 30 ml of 90% acetic acid and after the addition of 400 mg palladium on activated charcoal hydrogenated with hydrogen at 60° C. The catalyst is filtered off, the solution is evaporated down. The residue is chromatographed on silica gel and eluted with methanol. The desired fractions are evaporated down, triturated with ether, suction filtered and dried.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe solution is evaporated down
  3. customThe residue is chromatographed on silica gel
  4. washeluted with methanol
  5. customThe desired fractions are evaporated down
  6. customtriturated with ether, suction
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-7b189c8d243e48f5a7ac378b565d1f79
Source dataset
uspto-grants-2001_03
Patent number
US06200976B1

Reaction notes

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