Hydrochloric Acid → HCID 178437553, compound

HRID 653644Notes

Reaction equation

HRID 653644 reaction equation
C([N:8]1[C:12]2=[N:13][C:14]([C:18]([O:20][CH3:21])=[O:19])=[CH:15][C:16]([CH3:17])=[C:11]2[N:10]=[C:9]1[CH2:22][CH3:23])C1C=CC=CC=1.Cl>CO.[OH-].[OH-].[Pd+2]>[CH2:22]([C:9]1[N:8]=[C:12]2[NH:13][C:14]([C:18]([O:20][CH3:21])=[O:19])=[CH:15][C:16]([CH3:17])=[C:11]2[N:10]=1)[CH3:23]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 19385742Methyl 3-benzyl-2-ethyl-7-methylimidazo[4,5-b]pyridine-5-carboxylate

Product 1

HCID 178437553HCID 178437553, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of 750 mg of the crude product of Step F in MeOH (30 mL), concentration aqueous HCl (1 mL), and 100 mg of moist Pearlman's catalyst were shaken under 1 atm. H2 for 24 hours. The reaction was incomplete so 100 mg more of the catalyst was added and the reaction was shaken as described above for an additional 24 hours. Filtration, concentration, and extraction from dilute NH4OH with EtOAc followed by drying (Na2SO4), concentration, and purification (SiO2, 5 % MeOH/EtOAc) gave the title compound as a solid.

Workup

  1. additionwas added
  2. stirringthe reaction was shaken
  3. customas described above for an additional 24 hours
  4. filtrationFiltration, concentration, and extraction from dilute NH4OH with EtOAc
  5. customby drying
  6. concentration(Na2SO4), concentration, and purification (SiO2, 5 % MeOH/EtOAc)

Sources & evidence

ORD record
ord-35a9005879f047059f5450311077b5a1
Source dataset
uspto-grants-1992_07
Patent number
US05128327

Reaction notes

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