Trifluoroacetic acid → HCID 58259165, compound

HRID 509964Notes

Reaction equation

HRID 509964 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[N:7]=[C:8]([NH2:10])[CH:9]=1)=[O:4].[F:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=O)=[CH:23][CH:22]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>C(#N)C>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[N:7]=[C:8]([NH:10][CH2:25][C:24]2[CH:27]=[CH:28][C:21]([F:20])=[CH:22][CH:23]=2)[CH:9]=1)=[O:4]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 680234-FluorobenzaldehydeHCID 12073849HCID 12073849, compound

Product 1

HCID 58259165HCID 58259165, compoundYield 80.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a round bottom flask, 5-amino-2-(4-methoxy-benzyl)-2H-pyrazole-3-carboxylic acid methyl ester (109, 1.4 g, 5.4 mmol) was combined with 4-fluoro-benzaldehyde (110, 0.565 mL, 5.36 mmol), trifluoroacetic acid (2.06 mL, 26.8 mmol), triethylsilane (4.28 mL, 26.8 mmol) and 50 mL of acetonitrile. The reaction was stirred at room temperature for 15 minutes, then concentrated under vacuum, combined with aqueous potassium carbonate and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The residue was recrystallized from a mixture of ethyl acetate and hexane to provide the desired compound (111, 1.6 g). 1H NMR was consistent with the compound structure.

Workup

  1. concentrationconcentrated under vacuum
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under vacuum
  6. customThe residue was recrystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-464dff70865c468cb25fa79e0d579229
Source dataset
uspto-grants-2015_08
Patent number
US09096593B2

Reaction notes

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