Water → HCID 22485101, compound

HRID 2181049Notes

Reaction equation

HRID 2181049 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]([NH:7][C:8]1[CH:28]=[CH:27][C:11]([CH2:12][N:13]2[C:17]3=[N:18][C:19]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:21]=[C:16]3[N:15]=[C:14]2[CH3:26])=[C:10]([Cl:29])[CH:9]=1)=[O:6].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Cl:29][C:10]1[CH:9]=[C:8]([N:7]2[CH2:2][CH2:3][CH2:4][C:5]2=[O:6])[CH:28]=[CH:27][C:11]=1[CH2:12][N:13]1[C:17]2=[N:18][C:19]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:21]=[C:16]2[N:15]=[C:14]1[CH3:26]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 22485109HCID 22485109, compound

Product 1

HCID 22485101HCID 22485101, compoundYield 66.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Methyl 3-(4-((4-bromobutyryl)amino)-2-chlorobenzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylate (425 mg) was dissolved in N,N-dimethylformamide (5 ml) and potassium carbonate (245 mg) was added, which was followed by stirring at 60° C. for 2 hr. Water was added to the reaction mixture under ice-cooling and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Ethanol (10 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-oxotetrahydro-1H-pyrrol-1-yl)benzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylate (235 mg) as pale-yellow crystals.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed successively with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionEthanol (10 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-e42d3680ae6b46a09cb247c655c82119
Source dataset
uspto-grants-2005_05
Patent number
US06890934B2

Reaction notes

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