Hydrochloric Acid → 4-(1-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methylamino)-1-oxopropan-2-yl)-2-fluorobenzoic acid

HRID 1843039Notes

Reaction equation

HRID 1843039 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]([CH2:13][NH:14][C:15](=[O:27])[CH:16]([C:18]3[CH:23]=[CH:22]C(C#N)=[C:20]([F:26])[CH:19]=3)[CH3:17])=[CH:11][C:10]([C:28]([F:31])([F:30])[F:29])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[OH-:32].[Na+].Cl.[CH3:35][CH2:36][OH:37]>>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]([CH2:13][NH:14][C:15](=[O:27])[CH:16]([C:18]3[CH:23]=[CH:22][C:35]([C:36]([OH:32])=[O:37])=[C:20]([F:26])[CH:19]=3)[CH3:17])=[CH:11][C:10]([C:28]([F:31])([F:30])[F:29])=[N:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 70816495N-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-2-(4-cyano-3-fluorophenyl)propanamide

Product 1

HCID 708165544-(1-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methylamino)-1-oxopropan-2-yl)-2-fluorobenzoic acidYield 61%

Conditions

Temperature
100 °C

Procedure

To a solution compound N-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-2-(4-cyano-3-fluorophenyl)propanamide (870 mg, 1.930 mmol) in EtOH was added 2N NaOH (9.7 ml, 19.300 mmol). The reaction mixture was stirred overnight at 100° C. and then was cooled to room temperature. The mixture was acidified with 10% HCl solution and extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by column chromatography to give pure compound 4-(1-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methylamino)-1-oxopropan-2-yl)-2-fluorobenzoic acid (550 mg, 61%).

Workup

  1. temperaturewas cooled to room temperature
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-941a6007189b444e99ee0cc575e749d9
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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