Pentanenitrile, 4,4-dimethyl-3-oxo- → 3-(1,1-difluoroethyl)-1-(4-methoxyphenyl)-1H-pyrazol-5-amine

HRID 871703Notes

Reaction equation

HRID 871703 reaction equation
Cl.C[C:3]1[CH:8]=[C:7](C)[CH:6]=[CH:5][C:4]=1[NH:10][NH2:11].[F:12][C:13]([F:20])([CH3:19])[C:14](=O)[CH2:15][C:16]#[N:17].CC(C)(C)[C:23](=[O:27])CC#N>>[F:12][C:13]([C:14]1[CH:15]=[C:16]([NH2:17])[N:10]([C:4]2[CH:3]=[CH:8][C:7]([O:27][CH3:23])=[CH:6][CH:5]=2)[N:11]=1)([F:20])[CH3:19]

Participants

4

Reactant 3

HCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 162130592,4-Dimethylphenylhydrazine hydrochlorideHCID 86653534HCID 86653534, compound

Product 1

HCID 668758983-(1,1-difluoroethyl)-1-(4-methoxyphenyl)-1H-pyrazol-5-amineYield 11%

Procedure

Following the procedure for Example 282A Step 1, substituting p-methoxyphenylhydrazine for 2,4-dimethylphenylhydrazine hydrochloride and 4,4-difluoro-3-oxopentanenitrile was substituted for 4,4-Dimethyl-3-oxopentanenitrile. Concentration and purification using silica gel chromatography eluting with EtOAc/hexanes (5-40%) afforded 3-(1,1-difluoroethyl)-1-(4-methoxyphenyl)-1H-pyrazol-5-amine in 11% yield. LC-MS (ESI) m/z 254 (M+H)+.

Workup

  1. concentrationConcentration and purification
  2. washeluting with EtOAc/hexanes (5-40%)

Sources & evidence

ORD record
ord-fef92e49370c476888c5a840033c090c
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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