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

HRID 1257428Notes

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

Participants

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

temperaturewith heating
temperatureThe reaction mixture was cooled to room temperature
extractionthe mixture was extracted with ethyl acetate
dry with materialThe ethyl acetate layer was dried over sodium sulfate
concentrationconcentrated under reduced pressure
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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