Sodium Hydroxide → HCID 10075525, compound

HRID 490779Notes

Reaction equation

HRID 490779 reaction equation
C([O:3][C:4](=[O:39])[C:5]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH2:18][C:19]3[CH:20]=[N:21][N:22]([C:25]4[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[C:27]([C:35]([F:38])([F:37])[F:36])[CH:26]=4)[C:23]=3[CH3:24])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)([CH3:7])[CH3:6])C.[OH-].[Na+]>C(O)C>[F:37][C:35]([F:36])([F:38])[C:27]1[CH:26]=[C:25]([N:22]2[C:23]([CH3:24])=[C:19]([CH2:18][O:17][C:13]3[CH:12]=[C:11]4[C:16](=[CH:15][CH:14]=3)[N:8]([C:5]([CH3:6])([CH3:7])[C:4]([OH:39])=[O:3])[CH:9]=[CH:10]4)[CH:20]=[N:21]2)[CH:30]=[C:29]([C:31]([F:32])([F:33])[F:34])[CH:28]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86607977HCID 86607977, compound

Product 1

HCID 10075525HCID 10075525, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

2-{5-[1-(3,5-Bis-trifluoromethyl-phenyl)-5-methyl-1H-pyrazol-4-ylmethoxy]-indol-1-yl}-2-methyl-propionic acid ethyl ester from step A in ethanol (2 mL) is added NaOH (5.0 M, 1 mL). After heated at 50° C. for 2 hrs, ethanol is evaporated. The residue is diluted with water, acidified with 5 N HCl, extracted with ether, dried over sodium sulfate. Concentration and purification by reversed phase HPLC (acetone/water/TFA as eluents) yields the title compound (60 mg). MS (ES): 525.96(M+−1); the structure is also confirmed by 1H NMR.

Workup

  1. customethanol is evaporated
  2. additionThe residue is diluted with water
  3. extractionextracted with ether
  4. dry with materialdried over sodium sulfate
  5. concentrationConcentration and purification by reversed phase HPLC (acetone/water/TFA as eluents)

Sources & evidence

ORD record
ord-fc190f5651d942be8340d76edc5cfd82
Source dataset
uspto-grants-2009_05
Patent number
US07528160B2

Reaction notes

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