Trifluoroacetic acid → (3-tert-butyl-1-(4-fluorophenyl)-1H-pyrazol-5-yl)methanamine

HRID 1842933Notes

Reaction equation

HRID 1842933 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([CH2:10][NH:11]C(=O)OC(C)(C)C)[N:7]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[C:1]([C:5]1[CH:9]=[C:8]([CH2:10][NH2:11])[N:7]([C:19]2[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70855550tert-butyl (3-tert-butyl-1-(4-fluorophenyl)-1H-pyrazol-5-yl)methylcarbamate

Product 1

HCID 70815722(3-tert-butyl-1-(4-fluorophenyl)-1H-pyrazol-5-yl)methanamineYield 76.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 3 mL of dichloromethane, tert-butyl (3-tert-butyl-1-(4-fluorophenyl)-1H-pyrazol-5-yl)methylcarbamate (232 mg, 0.668 mmol, 1 equiv.) was dissolved and trifluoroacetic acid (0.496 mg, 0.331 ml, 6.5 equiv.) was added. The reaction mixture was stirred overnight at room temperature, extracted with aqueous sodium carbonate (c=1 mol/L), dried over magnesium sulfate and evaporated to give (3-tert-butyl-1-(4-fluorophenyl)-1H-pyrazol-5-yl)methanamine (127 mg) which was used without further purification.

Workup

  1. extractionextracted with aqueous sodium carbonate (c=1 mol/L)
  2. dry with materialdried over magnesium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-357a799e2f4d42eb87801fb636a95e12
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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