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Water → ethyl 1-({5-[3-(trifluoromethyl)phenyl]-1,3-oxazol-2-yl}methyl)-1H-pyrazole-4-carboxylate

HRID 1257428
Notes
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Reaction equation

HRID 1257428 reaction equation
[O:1]=[C:2]([NH:14][CH2:15][C:16](=O)[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=1)[CH2:3][N:4]1[CH:8]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[N:5]1.O>P(Cl)(Cl)(Cl)=O>[F:24][C:23]([F:26])([F:25])[C:19]1[CH:18]=[C:17]([C:16]2[O:1][C:2]([CH2:3][N:4]3[CH:8]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[N:5]3)=[N:14][CH:15]=2)[CH:22]=[CH:21][CH:20]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 962WaterHCID 58127653ethyl 1-[2-oxo-2-({2-oxo-2-[3-(trifluoromethyl)phenyl]ethyl}amino)ethyl]-1H-pyrazole-4-carboxylate

Product 1

HCID 58127502ethyl 1-({5-[3-(trifluoromethyl)phenyl]-1,3-oxazol-2-yl}methyl)-1H-pyrazole-4-carboxylateYield 71.9%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
120 °C

Procedure

The compound (0.73 g) obtained in Example 124a was dissolved in phosphorus oxychloride (10 mL), and the mixture was stirred at 110-130° C. overnight with heating. The reaction mixture was cooled to room temperature, slowly poured into water, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (carrier: silica gel, eluent: petroleum ether-ethyl acetate) to give the title compound (0.50 g) as a colorless solid.

Workup

  1. temperaturewith heating
  2. temperatureThe reaction mixture was cooled to room temperature
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe ethyl acetate layer was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography (carrier: silica gel, eluent: petroleum ether-ethyl acetate)

Sources & evidence

ORD record
ord-75ea3cf3293d4443b4cbd0de1df46330
Source dataset
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08461348B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes