Ethyl 2-[(2'-cyanobiphenyl-4-yl)methyl]-3-oxohexanoate → 4'-[(5-Oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)methyl]biphenyl-2-carbonitrile

HRID 1688394Notes

Reaction equation

HRID 1688394 reaction equation
[N:1]1[N:2]=[C:3]([NH2:6])[NH:4][CH:5]=1.[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH:22]([C:28](=O)[CH2:29][CH2:30][CH3:31])[C:23](OCC)=[O:24])=[CH:17][CH:16]=1)#[N:8]>ClC1C=CC(Cl)=CC=1Cl>[O:24]=[C:23]1[C:22]([CH2:21][C:18]2[CH:19]=[CH:20][C:15]([C:10]3[C:9]([C:7]#[N:8])=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:16][CH:17]=2)=[C:28]([CH2:29][CH2:30][CH3:31])[N:2]2[N:1]=[CH:5][N:4]=[C:3]2[NH:6]1

Participants

4

Reactant 2

HCID 10020734Ethyl 2-[(2'-cyanobiphenyl-4-yl)methyl]-3-oxohexanoateHCID 178509196HCID 178509196, compound

Product 1

HCID 1357150294'-[(5-Oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)methyl]biphenyl-2-carbonitrileYield 38%

Reagents, catalysts & solvents 1

HCID 131,2,4-TrichlorobenzeneSolvent

Procedure

A solution of 4H-1,2,4-triazol-3-amine (2.4 g) and ethyl 2-[(2′-cyanobiphenyl-4-yl)methyl]-3-oxohexanoate (10 g) in 1,2,4-trichlorobenzene (50 mL) was stirred at 180° C. for 6 hr. After evaporation of the solvent under reduced pressure, the residue was purified by silica gel column chromatography to give the title compound as a colorless solid (4 g, 38%).

Workup

  1. customAfter evaporation of the solvent under reduced pressure
  2. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-95897c819950450993d1b3722041ad15
Source dataset
uspto-grants-2012_04
Patent number
US08148383B2

Reaction notes

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