Water → HCID 86605788, compound

HRID 2221822Notes

Reaction equation

HRID 2221822 reaction equation
[CH2:1]([P:10](=[O:17])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])P(=O)(OCC)OCC.[H-].[Na+].[CH:20]([C:22]1[C:23]([NH:33][C:34](=[O:55])[C:35]2[CH:40]=[CH:39][C:38]([O:41][CH2:42][C:43]3[N:44]=[C:45]([C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=4)[O:46][C:47]=3[CH3:48])=[CH:37][CH:36]=2)=[N:24][N:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:26]=1)=O.O>CN(C)C=O>[CH3:48][C:47]1[O:46][C:45]([C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=2)=[N:44][C:43]=1[CH2:42][O:41][C:38]1[CH:39]=[CH:40][C:35]([C:34]([NH:33][C:23]2[C:22](/[CH:20]=[CH:1]/[P:10](=[O:17])([O:11][CH2:12][CH3:13])[O:14][CH2:15][CH3:16])=[CH:26][N:25]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:24]=2)=[O:55])=[CH:36][CH:37]=1

Participants

6

Reactant 4

HCID 962WaterHCID 15455Tetraethyl methylenediphosphonateHCID 24758Sodium hydrideHCID 86605789HCID 86605789, compound

Product 1

HCID 86605788HCID 86605788, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution (5 mL) of tetraethyl methylenediphosphonate (265 mg) in N,N-dimethylformamide was added sodium hydride (60% in oil, 40 mg) and the mixture was stirred at room temperature for 20 min. A solution (5 mL) of N-(4-formyl-1-phenyl-1H-pyrazol-3-yl)-4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]benzamide (400 mg) in N,N-dimethylformamide was added to the reaction mixture, and the mixture was 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 subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (1:1 to 1:0, v/v) to give diethyl (E)-2-[3-({4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]benzoyl}amino)-1-phenyl-1H-pyrazol-4-yl]ethenylphosphonate as colorless amorphous form (195 mg, yield 37%).

Workup

  1. stirringthe mixture was 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. washeluted with ethyl acetate-hexane (1:1 to 1:0

Sources & evidence

ORD record
ord-2bd0cfbd72c145efb68976b4e178b57f
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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