(4-Fluorophenyl)hydrazine → 3-tert-butyl-1-(4-fluorophenyl)-1H-pyrazol-5-amine

HRID 1094521Notes

Reaction equation

HRID 1094521 reaction equation
[C:1]([CH2:7][C:8]#[N:9])(=O)[C:2]([CH3:5])([CH3:4])[CH3:3].[F:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][NH2:18])=[CH:13][CH:12]=1>C1(C)C=CC=CC=1>[C:2]([C:1]1[CH:7]=[C:8]([NH2:9])[N:17]([C:14]2[CH:15]=[CH:16][C:11]([F:10])=[CH:12][CH:13]=2)[N:18]=1)([CH3:5])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 69982(4-Fluorophenyl)hydrazineHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-

Product 1

HCID 20605733-tert-butyl-1-(4-fluorophenyl)-1H-pyrazol-5-amine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The title compound is prepared according to a published literature procedure (see J. Med. Chem. 2002, 45, 2994-3008.): 4.17 g (32.3 mMol) of pivaloylacetonitrile are added to a solution of 4.20 g (32.3 mMol) 4-fluoro-phenylhydrazine in 150 ml of toluene at rt, and the resulting yellow solution is heated to and kept under reflux for 12 h. After completion, the reaction mixture is concentrated, and the resulting crude product is purified by flash chromatography (SiO2, 100% CH2Cl2) to give the title compound as a yellow solid: 1HNMR (CDCl3) δ ppm 7.59 (d, 2H), 7.10 (d, 2H), 5.58 (s, 1H), 3.62 (brs, H2N), 1.32 (s, 9H).

Workup

  1. customThe title compound is prepared
  2. temperaturethe resulting yellow solution is heated to and
  3. temperatureunder reflux for 12 h
  4. concentrationAfter completion, the reaction mixture is concentrated
  5. customthe resulting crude product is purified by flash chromatography (SiO2, 100% CH2Cl2)

Sources & evidence

ORD record
ord-006526648954493e8c61767b40d2db34
Source dataset
uspto-grants-2012_03
Patent number
US08133886B2

Reaction notes

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