Hydrochloric Acid → 1-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-4-(2,2,2-trifluoro-ethoxy)-1H-pyrazole-3,5-dicarboxylic acid 3-ethyl ester

HRID 33277Notes

Reaction equation

HRID 33277 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]([O:11][CH2:12][C:13]([F:16])([F:15])[F:14])=[C:9]([C:17]([O:19]CC)=[O:18])[N:8]([CH2:22][C:23](=[O:32])[NH:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][N:26]=2)[N:7]=1)=[O:5])[CH3:2].Cl>C1COCC1.[OH-].[Na+]>[CH2:1]([O:3][C:4]([C:6]1[C:10]([O:11][CH2:12][C:13]([F:14])([F:15])[F:16])=[C:9]([C:17]([OH:19])=[O:18])[N:8]([CH2:22][C:23](=[O:32])[NH:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][N:26]=2)[N:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 602079691-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-4-(2,2,2-trifluoro-ethoxy)-1H-pyrazole-3,5-dicarboxylic acid diethyl ester

Product 1

HCID 602079701-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-4-(2,2,2-trifluoro-ethoxy)-1H-pyrazole-3,5-dicarboxylic acid 3-ethyl ester

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 400 mg 1-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-4-(2,2,2-trifluoro-ethoxy)-1H-pyrazole-3,5-dicarboxylic acid diethyl ester in 5 ml THF and 0.9 ml 1N NaOH were added. After standing for 16 h, the solution was acidified using 1 N HCl to pH 1. The precipitating product was collected by filtration and dried under reduced pressure. Yield: 142 mg.

Workup

  1. filtrationThe precipitating product was collected by filtration
  2. customdried under reduced pressure

Sources & evidence

ORD record
ord-57c29de120fb4baaaa05701015f191c3
Source dataset
uspto-grants-2008_09
Patent number
US07429581B2

Reaction notes

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