Dimethylformamide → HCID 86605825, compound

HRID 2221870Notes

Reaction equation

HRID 2221870 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:44]=[CH:43][C:18]([C:19]([NH:21][C:22]2[C:26](/[CH:27]=[CH:28]/[P:29](=[O:36])([O:33][CH2:34][CH3:35])[O:30][CH2:31][CH3:32])=[CH:25][N:24]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[N:23]=2)=[O:20])=[CH:17][CH:16]=1.[H-].[Na+].[CH3:47]N(C)C=O.CI>O>[CH3:47][N:21]([C:19](=[O:20])[C:18]1[CH:43]=[CH:44][C:15]([O:14][CH2:13][C:3]2[N:4]=[C:5]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[O:6][C:2]=2[CH3:1])=[CH:16][CH:17]=1)[C:22]1[C:26](/[CH:27]=[CH:28]/[P:29](=[O:36])([O:33][CH2:34][CH3:35])[O:30][CH2:31][CH3:32])=[CH:25][N:24]([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[N:23]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86605788HCID 86605788, compound

Product 1

HCID 86605825HCID 86605825, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of diethyl (E)-2-[3-({4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]benzoyl}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 was 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. To remove remaining trifluoroacetic acid, water was added to the oil, 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-(methyl{4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]benzoyl}amino)-1-phenyl-1H-pyrazol-4-yl]ethenylphosphonate as a colorless oil (42.5 mg, yield 83%)

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 was 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
  8. customTo remove
  9. additionwas added to the oil
  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-bc77425d0cdc4cf4ae327d52cc26652e
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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