Ethanol → HCID 16128275, compound

HRID 2104247Notes

Reaction equation

HRID 2104247 reaction equation
C[O:2][C:3]([C:5]1([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)[CH2:10][CH2:9][N:8]([C:11](=[O:24])[CH2:12][N:13]2[C:17]([CH3:18])=[C:16]([Cl:19])[C:15]([C:20]([F:23])([F:22])[F:21])=[N:14]2)[CH2:7][CH2:6]1)=[O:4].CCO.[OH-].[Na+]>O>[Cl:19][C:16]1[C:15]([C:20]([F:23])([F:22])[F:21])=[N:14][N:13]([CH2:12][C:11]([N:8]2[CH2:7][CH2:6][C:5]([C:25]3[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][CH:30]=3)([C:3]([OH:4])=[O:2])[CH2:10][CH2:9]2)=[O:24])[C:17]=1[CH3:18]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 161282741-[2-(4-Chloro-5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetyl]-4-(4-chloro-phenyl)-piperidine-4-carboxylic acid methyl ester

Product 1

HCID 16128275HCID 16128275, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 4 mL vial was added 100 mg of 1-[2-(4-chloro-5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetyl]-4-(4-chloro-phenyl)-piperidine-4-carboxylic acid methyl ester (0.21 mmol, 1.0 equiv) and 400 mL EtOH. A solution of 9.2 mg of NaOH (0.23 mmol, 1.10 equiv) dissolved in 100 μL H2O was added to the reaction solution and the resultant mixture was stirred overnight at room temperature. The crude product was purified by reversed phase HPLC (acetonitrile—H2O with 0.1% TFA as the eluent) to yield 1-[2-(4-chloro-5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetyl]-4-(4-chloro-phenyl)-piperidine-4-carboxylic acid: MS (ES) M+H expected=464.3, found=464.1.

Workup

  1. additionwas added to the reaction solution
  2. customThe crude product was purified by reversed phase HPLC (acetonitrile—H2O with 0.1% TFA as the eluent)

Sources & evidence

ORD record
ord-dc362d44a47549a38c08784702a4d396
Source dataset
uspto-grants-2009_08
Patent number
US07576218B2

Reaction notes

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