Sodium Bicarbonate → HCID 178520290, compound

HRID 724142Notes

Reaction equation

HRID 724142 reaction equation
[NH2:1][C:2]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[C:15]([Cl:22])=[CH:14][C:3]=1[NH:4]C1C=CC=CC=1CCO.[NH:23]1[CH:27]=[CH:26][C:25]([CH:28]=O)=[N:24]1.[C:30]([O-:33])(=O)[CH3:31].[C:34]([O-])(=O)[CH3:35].[C:38]([O-])(=O)[CH3:39].[C:42]([O-])(=O)[CH3:43].[Pb+4].C(=O)([O-])O.[Na+]>C(O)C.C(OCC)(=O)C>[Cl:22][C:15]1[C:16]([C:18]([F:21])([F:19])[F:20])=[CH:17][C:2]2[N:1]=[C:28]([C:25]3[CH:26]=[CH:27][NH:23][N:24]=3)[N:4]([C:35]3[CH:34]=[CH:39][C:38]([CH2:31][CH2:30][OH:33])=[CH:43][CH:42]=3)[C:3]=2[CH:14]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 122183831H-Pyrazole-3-carbaldehydeHCID 21875690HCID 21875690, compoundHCID 178418268HCID 178418268, compound

Product 1

HCID 178520290HCID 178520290, compoundYield 84.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-(4-{[2-amino-5-chloro-4-(trifluoromethyl)phenyl]amino}phenyl)ethanol (step 2 of Example 104, 2.28 g, 5.85 mmol) and 1H-pyrazole-3-carbaldehyde (562 mg, 2.85 mmol) in ethanol (35 ml) was stirred under reflux temperature for 1 h. The mixture was concentrated and dissolved in benzene (40 ml). To this solution was added lead tetraacetate (2.85 g, 6.44 mmol) at rt. After stirring at room temperature for 18 h, to the mixture were added saturated aqueous sodium hydrogencarbonate (50 ml) and ethyl acetate. The organic layer was separated and washed with brine, dried (Na2SO4) and concentrated. Purification by flash column chromatography eluting with dichloromethane/methanol (20:1 to 10:1), then dichloromethane/2-propanol (5:1) afforded 979 mg (41%) of the title compound as a slight brown solid.

Workup

  1. temperatureunder reflux temperature for 1 h
  2. concentrationThe mixture was concentrated
  3. dissolutiondissolved in benzene (40 ml)
  4. stirringAfter stirring at room temperature for 18 h, to the mixture
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customPurification by flash column chromatography
  10. washeluting with dichloromethane/methanol (20:1 to 10:1)

Sources & evidence

ORD record
ord-e7e736dd8410458b9a3f0c6e72c4a9ed
Source dataset
uspto-grants-2006_11
Patent number
US07141580B2

Reaction notes

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