Hydrochloric Acid → (1-(4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanamine hydrochloride

HRID 1842876Notes

Reaction equation

HRID 1842876 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH2:13][NH:14]C(=O)OC(C)(C)C)=[CH:11][C:10]([C:22]([F:25])([F:24])[F:23])=[N:9]2)=[CH:4][CH:3]=1.[ClH:26]>O1CCOCC1>[ClH:26].[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH2:13][NH2:14])=[CH:11][C:10]([C:22]([F:24])([F:23])[F:25])=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 70855842tert-butyl (1-(4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methylcarbamate

Product 1

HCID 70816754(1-(4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanamine hydrochlorideYield 46%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

In 9 mL of dioxane, tert-butyl (1-(4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methylcarbamate (501 mg, 1.39 mmol) was dissolved and hydrogen chloride in dioxane (2.27 mL, c=4 mol/L, 9.06 mml, 6.5 equiv.) was added. The reaction mixture was stirred overnight and filtered, the filter cake was washed with ether (2×15 mL) and dried to give (1-(4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanamine hydrochloride (188 mg, 46%).

Workup

  1. filtrationfiltered
  2. washthe filter cake was washed with ether (2×15 mL)
  3. customdried

Sources & evidence

ORD record
ord-0d58b4c6d4d3410fa5845d021dfd996f
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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