Potassium Carbonate → HCID 58948129, compound

HRID 639597Notes

Reaction equation

HRID 639597 reaction equation
[CH:1]1([CH2:4][NH:5][C:6]([C:8]2[C:9]3[N:31]([CH2:32][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[C:30](=[O:39])[NH:29][C:10]=3[C:11]([N:14](CC3C=CC=CC=3)CC3C=CC=CC=3)=[N:12][CH:13]=2)=[O:7])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+]>S(=O)(=O)(O)O.O>[CH:1]1([CH2:4][NH:5][C:6]([C:8]2[C:9]3[N:31]([CH2:32][C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)[C:30](=[O:39])[NH:29][C:10]=3[C:11]([NH2:14])=[N:12][CH:13]=2)=[O:7])[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 67456561HCID 67456561, compound

Product 1

HCID 58948129HCID 58948129, compoundYield 14.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

1-benzyl-4-dibenzylamino-2-oxo-2,3-dihydro-1H-imidazo[4,5,c]pyridine-7-carboxylic acid cyclopropylmethyl-amide (10 mg, 0.02 mmol) was dissolved in 1 mL of concentrated sulphuric acid and the mixture was stirred at room temperature for 30 minutes. Once completed, the mixture was diluted in 5 mL of water and potassium carbonate was added portion wise until pH˜12. The mixture was then extracted with ethyl acetate (2×50 mL). The organic layers were combined, dried over MgSO4 and the solvent removed in vacuo. The residue was purified by column chromatography on silica gel using 20% of methanol in ethyl acetate to give 1 mg of the title compound.

Workup

  1. extractionThe mixture was then extracted with ethyl acetate (2×50 mL)
  2. dry with materialdried over MgSO4
  3. customthe solvent removed in vacuo
  4. customThe residue was purified by column chromatography on silica gel using 20% of methanol in ethyl acetate

Sources & evidence

ORD record
ord-5589ca6e1cea4181a6eadb366b5d1760
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

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