Trifluoroacetic acid → 5-Cyclopentylsulfanyl-1-(4-methoxycarbonylphenyl)pyrazole-4-carboxylic acid

HRID 1799424Notes

Reaction equation

FC(F)(F)C(O)=O.[CH:8]1([S:13][C:14]2[N:18]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([O:27][CH3:28])=[O:26])=[CH:21][CH:20]=3)[N:17]=[CH:16][C:15]=2[C:29]([O:31]C(C)(C)C)=[O:30])[CH2:12][CH2:11][CH2:10][CH2:9]1>C(Cl)Cl>[CH:8]1([S:13][C:14]2[N:18]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([O:27][CH3:28])=[O:26])=[CH:21][CH:20]=3)[N:17]=[CH:16][C:15]=2[C:29]([OH:31])=[O:30])[CH2:9][CH2:10][CH2:11][CH2:12]1

Participants

Conditions

Temperature: 20 °C

Procedure

Trifluoroacetic acid (2.63 mL, 34.29 mmol) was added to tert-butyl 5-(cyclopentylthio)-1-(4-(methoxycarbonyl)phenyl)-1H-pyrazole-4-carboxylate (Intermediate #94) (1.38 g, 3.43 mmol) in CH2Cl2 (25 mL) The resulting solution was stirred at 20° C. for 24 hours. The reaction mixture was evaporated to dryness, re-dissolved in dioxan (20 mL) and re-evaporated to dryness to afford 5-(cyclopentylthio)-1-(4-(methoxycarbonyl)phenyl)-1H-pyrazole-4-carboxylic acid (1.180 g, 99%) as a white to crystalline solid.

Workup

customThe reaction mixture was evaporated to dryness
dissolutionre-dissolved in dioxan (20 mL)
customre-evaporated to dryness

Sources & evidence

ORD record: ord-561ed55ea4fd47a9ba0fe00644730221
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08344016B2

Reaction notes

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