Sodium Hydroxide → HCID 57832742, compound

HRID 729473Notes

Reaction equation

HRID 729473 reaction equation
[F:1][C:2]([F:34])([F:33])[C:3]1[CH:32]=[CH:31][CH:30]=[CH:29][C:4]=1[O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[N:17]=[CH:16][C:15]([C:18]3[CH:19]=[N:20][N:21]([CH2:23][C:24]([O:26]CC)=[O:25])[CH:22]=3)=[CH:14][N:13]=2)[CH2:8][CH2:7]1.[OH-].[Na+]>CO>[F:34][C:2]([F:1])([F:33])[C:3]1[CH:32]=[CH:31][CH:30]=[CH:29][C:4]=1[O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[N:17]=[CH:16][C:15]([C:18]3[CH:19]=[N:20][N:21]([CH2:23][C:24]([OH:26])=[O:25])[CH:22]=3)=[CH:14][N:13]=2)[CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86621806HCID 86621806, compound

Product 1

HCID 57832742HCID 57832742, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

Into a 10-mL flask equipped with a magnetic stirbar was added ethyl [4-(2-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}pyrimidin-5-yl)-1H-pyrazol-1-yl]acetate-(50 mg, 0.10 mmol), methanol (2 mL) and 1 M aqueous sodium hydroxide solution (0.52 mL, 0.53 mmol). The suspension was heated to 80° C. for 2 h. The reaction mixture was concentrated to remove the methanol and the residue was poured into a 125-mL separatory funnel containing saturated aqueous KH2PO4 solution (75 mL) and the mixture was extracted with ethyl acetate (3×30 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and the solvent was evaporated under reduced pressure to give the desired product.

Workup

  1. customInto a 10-mL flask equipped with a magnetic stirbar
  2. concentrationThe reaction mixture was concentrated
  3. customto remove the methanol
  4. additionthe residue was poured into a 125-mL separatory funnel
  5. additioncontaining saturated aqueous KH2PO4 solution (75 mL)
  6. extractionthe mixture was extracted with ethyl acetate (3×30 mL)
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f2ea88af2c234de894a504cfeb948db3
Source dataset
uspto-grants-2009_09
Patent number
US07582633B2

Reaction notes

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