Water → HCID 86605794, compound

HRID 2221832Notes

Reaction equation

HRID 2221832 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:58])[CH2:35][C:36]2[CH:41]=[CH:40][C:39]([O:42][CH2:43][C:44]3[N:45]=[C:46]([C:50]4[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=4)[O:47][C:48]=3[CH3:49])=[C:38]([O:56][CH3:57])[CH:37]=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>[CH3:57][O:56][C:38]1[CH:37]=[C:36]([CH2:35][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:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:24]=2)=[O:58])[CH:41]=[CH:40][C:39]=1[O:42][CH2:43][C:44]1[N:45]=[C:46]([C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=2)[O:47][C:48]=1[CH3:49]

Participants

6

Reactant 4

HCID 962WaterHCID 15455Tetraethyl methylenediphosphonateHCID 24758Sodium hydrideHCID 86605795HCID 86605795, compound

Product 1

HCID 86605794HCID 86605794, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of tetraethyl methylenediphosphonate (357 mg) in N,N-dimethylformamide (5 mL) was added sodium hydride (60% in oil, 54 mg), and the mixture was stirred at room temperature for 20 min. To the reaction mixture was added a solution of N-(4-formyl-1-phenyl-1H-pyrazol-3-yl)-2-{3-methoxy-4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl}acetamide (590 mg) in N,N-dimethylformamide (5 mL), 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-[({3-methoxy-4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl}acetyl)amino]-1-phenyl-1H-pyrazol-4-yl}ethenylphosphonate as colorless amorphous form (159 mg, yield 21%).

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-ac7a253e076b45afb61294be15f204f9
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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