Hydrochloric Acid → 1-[1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-1H-pyrazole-3-carboxylic acid

HRID 2043763Notes

Reaction equation

[CH3:1][C:2]1[N:6]([CH2:7][C:8]([N:10]2[CH2:15][CH2:14][CH:13]([N:16]3[CH:20]=[CH:19][C:18]([C:21]([O:23]C)=[O:22])=[N:17]3)[CH2:12][CH2:11]2)=[O:9])[N:5]=[C:4]([C:25]([F:28])([F:27])[F:26])[CH:3]=1.[OH-].[Na+].Cl.[Cl-].[Na+]>CO>[CH3:1][C:2]1[N:6]([CH2:7][C:8]([N:10]2[CH2:15][CH2:14][CH:13]([N:16]3[CH:20]=[CH:19][C:18]([C:21]([OH:23])=[O:22])=[N:17]3)[CH2:12][CH2:11]2)=[O:9])[N:5]=[C:4]([C:25]([F:28])([F:26])[F:27])[CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of methyl 1-[1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-1H-pyrazole-3-carboxylate (320 mg, 0.8 mmol) (i.e. the product of Example 18, Step D) in 8 mL of methanol was cooled to 0° C. and 1 M aqueous sodium hydroxide solution (1.6 mL, 1.6 mmol) was gradually added. The reaction mixture was stirred at 50° C. for 16 h, and 1 M aqueous hydrochloric acid (1.6 mL, 1.6 mmol) was added followed by 5 mL of saturated aqueous solution of sodium chloride. The resulting mixture was extracted with ethyl acetate, and the extract was dried over magnesium sulfate and evaporated in vacuo to give 270 mg of the title compound as a glassy solid.

Workup

extractionThe resulting mixture was extracted with ethyl acetate
dry with materialthe extract was dried over magnesium sulfate
customevaporated in vacuo

Sources & evidence

ORD record: ord-a9064b33c2084552bdedc3a401e35763
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586611B2

Reaction notes

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