Methyl iodide → HCID 67267649, compound

HRID 598200Notes

Reaction equation

HRID 598200 reaction equation
[CH2:1]([NH:7][C:8]([N:10]1[C:18]2[C:13](=[N:14][CH:15]=[CH:16][CH:17]=2)[NH:12][C:11]1=[O:19])=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].IC.[C:22](=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:1]([NH:7][C:8]([N:10]1[C:18]2[C:13](=[N:14][CH:15]=[CH:16][CH:17]=2)[N:12]([CH3:22])[C:11]1=[O:19])=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 67267642HCID 67267642, compound

Product 1

HCID 67267649HCID 67267649, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 2.5 ml of DMF, N-hexyl-2-oxo-2,3-dihydroimidazo[4,5-b]pyridine-1-carboxamide (65 mg, 0.248 mmol), iodomethane (70 mg, 0.5 mmol) and cesium carbonate (80 mg, 0.25 mmol) were stirred at RT for 5 h. After concentration, the mixture was admixed with water and ethyl acetate, and the organic phase was removed, concentrated and purified by means of preparative HPLC (PR18, acetonitrile/water 0.1% TFA). Yield: 16 mg (23%), M+H+: 277.17.

Workup

  1. concentrationAfter concentration
  2. customthe organic phase was removed
  3. concentrationconcentrated
  4. custompurified by means of preparative HPLC (PR18, acetonitrile/water 0.1% TFA)

Sources & evidence

ORD record
ord-8fba65cd3c0e469190e290a0b1f55d5d
Source dataset
uspto-grants-2011_03
Patent number
US07897616B2

Reaction notes

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