benzyl N'-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridine-2-carbonyl]hydrazinecarboxylate → 6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridine-2-carbohydrazide

HRID 71182Notes

Reaction equation

HRID 71182 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]([NH:11][NH:12]C(OCC2C=CC=CC=2)=O)=[O:10])[CH:6]=[CH:5][C:4]=1[N:23]1[CH:27]=[C:26]([CH3:28])[N:25]=[CH:24]1>CO.C1COCC1.[C].[Pd]>[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]([NH:11][NH2:12])=[O:10])[CH:6]=[CH:5][C:4]=1[N:23]1[CH:27]=[C:26]([CH3:28])[N:25]=[CH:24]1

Participants

5

Reactant 1

HCID 66608695benzyl N'-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridine-2-carbonyl]hydrazinecarboxylate

Product 1

HCID 666083826-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridine-2-carbohydrazideYield 41.2%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, to a mixture of benzyl 2-{[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]carbonyl}hydrazinecarboxylate (14.6 g) in methanol (150 mL) and THF (100 mL) was added 5% palladium-carbon (1.5 g) at room temperature, and the mixture was stirred at room temperature for 6 hr under a hydrogen atmosphere. Under a nitrogen atmosphere, the catalyst was filtered off, and the solvent in the filtrate was evaporated under reduced pressure. To a mixture of the residue in ethanol (200 mL) and THF (400 mL) was added 5% palladium-carbon (1.5 g) at room temperature, and the mixture was stirred at room temperature overnight under a hydrogen atmosphere. Under a nitrogen atmosphere, the catalyst was filtered off, and the solvent in the filtrate was evaporated under reduced pressure. The residue was collected by filtration, washed with ethyl acetate and dried to give the title compound (3.9 g). The solvent in the mother liquor was evaporated under reduced pressure, and the residue was collected by filtration, washed with ethyl acetate and dried to give the title compound (2.6 g).

Workup

  1. filtrationUnder a nitrogen atmosphere, the catalyst was filtered off
  2. customthe solvent in the filtrate was evaporated under reduced pressure
  3. additionTo a mixture of the residue in ethanol (200 mL)
  4. additionTHF (400 mL) was added 5% palladium-carbon (1.5 g) at room temperature
  5. stirringthe mixture was stirred at room temperature overnight under a hydrogen atmosphere
  6. filtrationUnder a nitrogen atmosphere, the catalyst was filtered off
  7. customthe solvent in the filtrate was evaporated under reduced pressure
  8. filtrationThe residue was collected by filtration
  9. washwashed with ethyl acetate
  10. customdried

Sources & evidence

ORD record
ord-6656422d4c90482baade7935fbeda0c2
Source dataset
uspto-grants-2014_09
Patent number
US08822699B2

Reaction notes

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