Water → HCID 22241628, compound

HRID 892012Notes

Reaction equation

HRID 892012 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][N:13]=[C:12]2[CH2:18][C:19](=[O:21])[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.IC.[C:24](=O)([O-])[O-].[K+].[K+].O>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:24])[N:13]=[C:12]2[CH2:18][C:19](=[O:21])[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178467665HCID 178467665, compound

Product 1

HCID 22241628HCID 22241628, compoundYield 47.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of the product from Step A (1.2 g, 4.28 mmol) in DMF (10 ml) was added iodomethane (0.53 ml, 8.6 mmol) and potassium carbonate (1.2 g, 8.6 mmol); this mixture was stirred for 16 h at 70° C. After adding water (15 ml) and ethyl acetate (15 ml) to the reaction mixture, the aqueous layer was separated and extracted with ethyl acetate (3×20 ml). The combined extracts were washed with brine, dried (MgSO4), and evaporated to a residue which was puified by chromatography (silica, ethyl acetate/hexane, 1:1) to give a viscous oil (0.6 g): APCl/LCMS m/z 295 (M+H)+.

Workup

  1. customthe aqueous layer was separated
  2. extractionextracted with ethyl acetate (3×20 ml)
  3. washThe combined extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated to a residue which

Sources & evidence

ORD record
ord-9dd87f58283a4d8eade06778c3505f70
Source dataset
uspto-grants-2006_02
Patent number
US07005443B1

Reaction notes

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