Sodium Hydroxide → HCID 59547946, compound

HRID 1946311Notes

Reaction equation

HRID 1946311 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]([NH:11][C:12]1[CH:16]=[CH:15][N:14]([CH2:17][C:18]2[CH:28]=[CH:27][C:21]([C:22]([O:24]CC)=[O:23])=[CH:20][C:19]=2[C:29]([F:32])([F:31])[F:30])[N:13]=1)=[O:10].[OH-].[Na+]>CO>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]([NH:11][C:12]1[CH:16]=[CH:15][N:14]([CH2:17][C:18]2[CH:28]=[CH:27][C:21]([C:22]([OH:24])=[O:23])=[CH:20][C:19]=2[C:29]([F:32])([F:30])[F:31])[N:13]=1)=[O:10]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59547919HCID 59547919, compound

Product 1

HCID 59547946HCID 59547946, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl 4-[(3-{[(2,6-difluorophenyl)carbonyl]amino}-1H-pyrazol-1-yl)methyl]-3-(trifluoromethyl)benzoate (for a preparation see Example 43)(0.773 g, 1.71 mmol) in methanol (20 ml) was added 2 M aqueous sodium hydroxide (5 ml, 10 mmol). The solution was heated to 60° C. under air for 45 min. The solvent was removed at reduced pressure and the residue dissolved in water (50 ml). The solution was acidified using 2M HCl aqueous (10 ml). The suspension was diluted with ethyl acetate (50 ml) and the phases separated. The aqueous phase was extracted with ethyl acetate (25 ml). The combined organic extracts were dried (MgSO4), filtered and the solvent removed in vacuo to give the title compound as a white solid (0.666 g); LCMS: (System 4) MH+=426, tRET=2.48 min.

Workup

  1. customThe solvent was removed at reduced pressure
  2. dissolutionthe residue dissolved in water (50 ml)
  3. additionThe suspension was diluted with ethyl acetate (50 ml)
  4. customthe phases separated
  5. extractionThe aqueous phase was extracted with ethyl acetate (25 ml)
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-0da96fc7d8e2455e91ae25d355be9fde
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

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