HCID 178514299, compound → HCID 178478064, compound

HRID 861048Notes

Reaction equation

HRID 861048 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)C1C=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][CH2:8][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 178478064HCID 178478064, compoundYield 121.9%

Reagents, catalysts & solvents 1

HCID 7504BenzylamineSolvent

Procedure

A solution of the bromopyridine compound prepared in step 3 of Example A-219 (150 mg, 0.5 mmol) in benzylamine (5 ml) was heated at 175° C. for six hours. After cooling, excess benzylamine was removed by high vacuum distillation and ethyl acetate added to the residue. After washing the organic phase with water and drying over magnesium sulfate, the solvent was removed in vacuo and the residue chromatographed on silica gel using mixtures of ethyl acetate and toluene to give 4-[3-(3-chlorophenyl)-1H-pyrazol-4-yl]-N-(phenylmethyl)-2-pyridinamine (110 mg, 61%) as a solid, m.p. 179–180° C.

Workup

  1. temperatureAfter cooling
  2. customexcess benzylamine was removed by high vacuum distillation and ethyl acetate
  3. additionadded to the residue
  4. washAfter washing the organic phase with water
  5. dry with materialdrying over magnesium sulfate
  6. customthe solvent was removed in vacuo
  7. customthe residue chromatographed on silica gel using mixtures of ethyl acetate and toluene

Sources & evidence

ORD record
ord-72419b815d8a41e5a377c525774ca77c
Source dataset
uspto-grants-2006_12
Patent number
US07153959B2

Reaction notes

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