HCID 178514299, compound → HCID 178478064, compound

HRID 1167525Notes

Reaction equation

HRID 1167525 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-154c007f2c064072a7bc3858be8c6366
Source dataset
uspto-grants-2003_09
Patent number
US06617324B1

Reaction notes

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