Hydrochloric Acid → HCID 22485019, compound

HRID 1368258Notes

Reaction equation

HRID 1368258 reaction equation
[Cl:1][C:2]1[CH:22]=[C:21]([NH:23][C:24]([O:26][CH2:27][CH2:28]Cl)=[O:25])[CH:20]=[CH:19][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:13]=[C:8]2[N:7]=[C:6]1[CH3:18].C[O-].[Na+].Cl.C(=O)([O-])O.[Na+]>CO>[Cl:1][C:2]1[CH:22]=[C:21]([N:23]2[CH2:28][CH2:27][O:26][C:24]2=[O:25])[CH:20]=[CH:19][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:13]=[C:8]2[N:7]=[C:6]1[CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 10942334Sodium MethoxideHCID 22485139HCID 22485139, compound

Product 1

HCID 22485019HCID 22485019, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
60 °C

Procedure

Methyl 3-(2-chloro-4-((2-chloroethoxycarbonyl)amino)-benzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylate (240 mg) was dissolved in methanol (3 ml) and a 28% solution (159 mg) of sodium methylate in methanol was added at room temperature, which was followed by stirring at 60° C. for 2 hr. The reaction mixture was neutralized with 1N hydrochloric acid under ice-cooling. A saturated aqueous sodium hydrogen carbonate solution was added and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Ethyl acetate (5 ml) was added to the residue and the mixture was heated and allowed to cool. The precipitated crystals were collected by filtration and dried under reduced pressure with heating to give methyl 3-(2-chloro-4-(2-oxo-1,3-oxazolidin-3-yl)benzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylate (121 mg) as yellow crystals.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with chloroform
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionEthyl acetate (5 ml) was added to the residue
  7. temperaturethe mixture was heated
  8. temperatureto cool
  9. filtrationThe precipitated crystals were collected by filtration
  10. customdried under reduced pressure
  11. temperaturewith heating

Sources & evidence

ORD record
ord-b8ad4851bb284362802eebf28532c003
Source dataset
uspto-grants-2003_06
Patent number
US06573274B1

Reaction notes

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