Dimethylformamide → HCID 86605858, compound

HRID 2221916Notes

Reaction equation

HRID 2221916 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:45])=[C:9]([CH2:11][O:12][C:13]2[CH:42]=[CH:41][C:16]([C:17]([NH:19][C:20]3[C:24](/[CH:25]=[CH:26]/[P:27](=[O:34])([O:31][CH2:32][CH3:33])[O:28][CH2:29][CH3:30])=[CH:23][N:22]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[N:21]=3)=[O:18])=[CH:15][C:14]=2[O:43][CH3:44])[N:10]=1.[H-].[Na+].[CH3:48]N(C)C=O.CI>O>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:45])=[C:9]([CH2:11][O:12][C:13]2[CH:42]=[CH:41][C:16]([C:17]([N:19]([CH3:48])[C:20]3[C:24](/[CH:25]=[CH:26]/[P:27](=[O:34])([O:28][CH2:29][CH3:30])[O:31][CH2:32][CH3:33])=[CH:23][N:22]([C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)[N:21]=3)=[O:18])=[CH:15][C:14]=2[O:43][CH3:44])[N:10]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86605809HCID 86605809, compound

Product 1

HCID 86605858HCID 86605858, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of diethyl (E)-2-{3-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy)-3-methoxybenzoyl)amino]-1-phenyl-1H-pyrazol-4-yl}ethenylphosphonate (50 mg), sodium hydride (60% in oil, 3.9 mg) and N,N-dimethylformamide (2 mL) was added methyl iodide (14 mg) with stirring, and the mixture was further stirred at room temperature for 2 hrs. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer as washed successively with distilled water and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by reverse phase partition-high performance liquid chromatography (elution with distilled water containing 0.1% trifluoroacetic acid/acetonitrile) to give a colorless oil compound. To remove remaining trifluoroacetic acid, water was added to the oil compound, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous magnesium sulfate and concentrated to give diethyl (E)-2-{3-[(4-([2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzoyl)(methyl)amino]-1-phenyl-1H-pyrazol-4-yl}ethenylphosphonate as a colorless oil (39.8 mg, yield 78%).

Workup

  1. stirringthe mixture was further stirred at room temperature for 2 hrs
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer as washed successively with distilled water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. distillationThe residue was purified by reverse phase partition-high performance liquid chromatography (elution with distilled water containing 0.1% trifluoroacetic acid/acetonitrile)
  7. customto give a colorless oil compound
  8. customTo remove
  9. additionwas added to the oil compound
  10. extractionthe mixture was extracted with ethyl acetate
  11. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-8b9505930da14eb2835cb7b139cfcec3
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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