3-amino-5-butyl-4-[(2'-cyanobiphenyl-4-yl)methyl]-4H-1,2,4-triazole → 2-Butyl-3-[(2'-cyanobiphenyl-4-yl)methyl]-6-phenyl-3H-imidazo[1,2-b][1,2,4]triazole

HRID 2082066Notes

Reaction equation

HRID 2082066 reaction equation
[NH2:1][C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[C:20]#[N:21])=[CH:10][CH:9]=2)[C:5]([CH2:22][CH2:23][CH2:24][CH3:25])=[N:4][N:3]=1.Br[CH:27]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH:28]=O>C(O)C>[CH2:22]([C:5]1[N:6]([CH2:7][C:8]2[CH:9]=[CH:10][C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[C:20]#[N:21])=[CH:12][CH:13]=2)[C:2]2[N:3]([C:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:28][N:1]=2)[N:4]=1)[CH2:23][CH2:24][CH3:25]

Participants

4

Reactant 2

HCID 100652943-amino-5-butyl-4-[(2'-cyanobiphenyl-4-yl)methyl]-4H-1,2,4-triazoleHCID 108889012-Bromo-2-phenylacetaldehyde

Product 1

HCID 104105022-Butyl-3-[(2'-cyanobiphenyl-4-yl)methyl]-6-phenyl-3H-imidazo[1,2-b][1,2,4]triazoleYield 24%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 212 mg (0.640 mmole) of 3-amino-5-butyl-4-[(2'-cyanobiphenyl-4-yl)methyl]-4H-1,2,4-triazole (from Example 1, Step D), 151 mg (0.757 mmol) of α-bromophenylacetaldehyde [T. L. Jacobs and W. R. Scott, Jr., J. Am. Chem. Soc., 75, 5500 (1953)], and 2.0 ml of absolute ethanol was stirred at reflux under N2 for 6 hours. The mixture was cooled and concentrated in vacuo. The residue was chromatographed on a column of silica gel (27×2.5 cm) packed in CH2Cl2 (elution with 1% and then 4% MeOH in CH2Cl2). Concentration of the appropriate pooled product fractions afforded 65.3 mg (24%) of the title compound as a yellow oil; homogeneous by TLC in 19:1 CH2Cl2 -MeOH.

Workup

  1. temperatureat reflux under N2 for 6 hours
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated in vacuo
  4. customThe residue was chromatographed on a column of silica gel (27×2.5 cm)
  5. washelution with 1%

Sources & evidence

ORD record
ord-3a2e287b8c5d4f2c8f1cb3e58408daac
Source dataset
uspto-grants-1993_02
Patent number
US05187179

Reaction notes

Loading…