Hydrochloric Acid → 5-(trifluoromethyl)-1-({4-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}methyl)-1H-pyrazole-4-carboxylic acid

HRID 1257410Notes

Reaction equation

HRID 1257410 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[N:7]([CH2:8][C:9]2[S:10][CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=3)[N:13]=2)[N:6]=[CH:5][C:4]=1[C:24]([O:26]CC)=[O:25].[OH-].[Na+].C(O)C.Cl>O.C(OCC)(=O)C.O1CCCC1>[F:30][C:2]([F:1])([F:29])[C:3]1[N:7]([CH2:8][C:9]2[S:10][CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=3)[N:13]=2)[N:6]=[CH:5][C:4]=1[C:24]([OH:26])=[O:25]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 86650597ethyl 5-(trifluoromethyl)-1-({4-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}methyl)-1H-pyrazole-4-carboxylate

Product 1

HCID 866505985-(trifluoromethyl)-1-({4-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}methyl)-1H-pyrazole-4-carboxylic acidYield 98.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the compound (0.13 g) obtained in Example 103d, 4N sodium hydroxide (1 mL), ethanol (2 mL) and tetrahydrofuran (0.5 mL) was stirred at room temperature for 20 hr. The reaction mixture was adjusted to pH 5 with 1N hydrochloric acid, and ethyl acetate and water were added. The ethyl acetate layer was separated, dried over sodium sulfate, and concentrated under reduced pressure to give the title compound (0.12 g) as colorless crystals.

Workup

  1. additionwere added
  2. customThe ethyl acetate layer was separated
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ab95609c0d4a4112886b0f29930c2cf8
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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