4-Bromobenzyl bromide → YM511 (pharmaceutical)

HRID 1488494Notes

Reaction equation

HRID 1488494 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][N:10]2[CH:14]=[N:13][N:12]=[CH:11]2)=[CH:5][CH:4]=1)#[N:2].[Br:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Br)=[CH:18][CH:17]=1>C(#N)C>[Br:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][N:9]([N:10]2[CH:11]=[N:12][N:13]=[CH:14]2)[C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=2)=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 685274-Bromobenzyl bromideHCID 10307909Benzonitrile, 4-(4H-1,2,4-triazol-4-ylamino)-

Product 1

HCID 177865YM511 (pharmaceutical)Yield 65.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

40 Milliliters of acetonitrile was added to 3.15 g of 4-[N-(4-cyanophenyl)amino]-4H-1,2,4-triazole, 4.25 g of 4-bromobenzyl bromide and 3.52 g of anhydride potassium carbonate and the mixture was stirred for 2 hours at room temperature. The solvent was removed by distillation under reduced pressure, and water was added to the residue formed, which was then extracted with chloroform. The chloroform layer separated was washed with water and dried over anhydrous magnesium sulfate, and the solvent was removed by distillation. The residue was purified by silica gel column chromatography to give crude crystals from the chloroform/methanol (100/1) eluate. The crude crystals were recrystallized from ethanol to give 3.92 g of 4-[N-(4-bromobenzyl)-N-(4-cyanophenyl)amino]-4H-1,2,4-triazole.

Workup

  1. customThe solvent was removed by distillation under reduced pressure, and water
  2. additionwas added to the residue
  3. customformed
  4. extractionwhich was then extracted with chloroform
  5. customThe chloroform layer separated
  6. washwas washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was removed by distillation
  9. customThe residue was purified by silica gel column chromatography
  10. customto give crude crystals from the chloroform/methanol (100/1) eluate
  11. customThe crude crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-8bc7e8852bb74693bdf7708b3b2669e7
Source dataset
uspto-grants-1997_10
Patent number
US05674886

Reaction notes

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