HCID 60209557, compound → HCID 60209558, compound

HRID 1640411Notes

Reaction equation

HRID 1640411 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][CH2:19][C:20]([NH:22][CH3:23])=[O:21])=[O:17])[CH2:12][CH2:11]2)=[N:8][CH:9]=1)([O-])=O>[Pd].C(OCC)(=O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:11][CH2:12][N:13]([C:16]([O:18][CH2:19][C:20]([NH:22][CH3:23])=[O:21])=[O:17])[CH2:14][CH2:15]2)=[N:8][CH:9]=1

Participants

4

Reactant 1

HCID 60209557HCID 60209557, compound

Product 1

HCID 60209558HCID 60209558, compoundYield 80.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

0.24 g of 10% palladium on charcoal is added to a suspension of 0.64 g (1.98 mmol) of 2-(methylamino)-2-oxoethyl 4-(5-nitro-2-pyridyl)-1-piperazinecarboxylate, prepared in step 5.3, in 90 ml of ethyl acetate. Stirring is continued at room temperature under a hydrogen atmosphere of 60 psi for 14 hours. After filtering off the catalyst, the filtrate is concentrated under reduced pressure and the residue thus obtained is purified by chromatography on silica gel, eluting with a 98/2 mixture of dichloromethane and methanol. 0.47 g of product is obtained in the form of a violet-colored oil, and is used without further purification in the following step.

Workup

  1. filtrationAfter filtering off the catalyst
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customthe residue thus obtained
  4. customis purified by chromatography on silica gel
  5. washeluting with a 98/2 mixture of dichloromethane and methanol

Sources & evidence

ORD record
ord-78aa949a13e04497afa234f3077eb264
Source dataset
uspto-grants-2012_02
Patent number
US08114866B2

Reaction notes

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