Hydrochloric Acid → [4-(5-Methyl-3-trifluoromethyl-1H-pyrazol-4-yl)-phenyl]-acetonitrile

HRID 45512Notes

Reaction equation

HRID 45512 reaction equation
[CH3:1][C:2]1[N:6](C2CCCCO2)[N:5]=[C:4]([C:13]([F:16])([F:15])[F:14])[C:3]=1[C:17]1[CH:22]=[CH:21][C:20]([CH2:23][C:24]#[N:25])=[CH:19][CH:18]=1.Cl>C(OCC)(=O)C>[CH3:1][C:2]1[NH:6][N:5]=[C:4]([C:13]([F:16])([F:15])[F:14])[C:3]=1[C:17]1[CH:22]=[CH:21][C:20]([CH2:23][C:24]#[N:25])=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59331959{4-[5-Methyl-1-(tetrahydro-pyran-2-yl)-3-trifluoromethyl-1H-pyrazol-4-yl]-phenyl}-acetonitrile

Product 1

HCID 59331945[4-(5-Methyl-3-trifluoromethyl-1H-pyrazol-4-yl)-phenyl]-acetonitrile

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To {4-[5-Methyl-1-(tetrahydro-pyran-2-yl)-3-trifluoromethyl-1H-pyrazol-4-yl]-phenyl}-acetonitrile (Example 8B) (35 mg, 0.1 mmol, 1.0 equiv) in ethyl acetate (1 ml) was added HCl in ethyl acetate (1 ml) and the mixture was stirred for 1 hour. The solvents were removed under reduced pressure and the title compound was purified by column chromatography (SiO2) eluting with a linear gradient (0→30% ethyl acetate-petrol) 16 mg (60%); LCMS (PS-A) Rt 2.85 min [M+H]+ 266.

Workup

  1. customThe solvents were removed under reduced pressure
  2. customthe title compound was purified by column chromatography (SiO2)
  3. washeluting with a linear gradient (0→30% ethyl acetate-petrol) 16 mg (60%)

Sources & evidence

ORD record
ord-df415bfe61514465839a325e732b5b76
Source dataset
uspto-grants-2013_09
Patent number
US08541461B2

Reaction notes

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