HCID 178514299, compound → HCID 178478065, compound

HRID 1167526Notes

Reaction equation

HRID 1167526 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][NH:16][C:15](=[N:19]N)[CH:14]=3)=[CH:11][NH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1>C(N)CC1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([NH:19][CH2:12][CH2:8][C:4]4[CH:5]=[CH:6][CH:7]=[CH:2][CH:3]=4)[CH:14]=3)=[CH:11][NH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 178514299HCID 178514299, compound

Product 1

HCID 178478065HCID 178478065, compoundYield 163.6%

Reagents, catalysts & solvents 1

HCID 1001PhenethylamineSolvent

Procedure

A solution of the bromopyridine compound prepared in step 3 of Example A-219 (250 mg, 0.75 mmol) in phenethylamine (5 ml) was heated at 175° C. for six hours under a nitrogen atmosphere. The excess amine was distilled off under high vacuum and the residue was dissolved in ethyl acetate and washed with water. After drying over magnesium sulfate and removal of solvent, the residue was chromatographed on silica gel with mixtures of ethyl acetate and toluene to give 4-[3-(3-chlorophenyl)-1H-pyrazol-4-yl]-N-(phenylethyl)-2-pyridinamine (230 mg, 81%) as a solid, m.p. 185-186° C.

Workup

  1. distillationThe excess amine was distilled off under high vacuum
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with water
  4. dry with materialAfter drying over magnesium sulfate and removal of solvent
  5. customthe residue was chromatographed on silica gel with mixtures of ethyl acetate and toluene

Sources & evidence

ORD record
ord-85cc24062e7b4c7fb74532ea63d39bf0
Source dataset
uspto-grants-2003_09
Patent number
US06617324B1

Reaction notes

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