Methyl 2-[(2'-cyanobiphenyl-4-yl)methyl]-3-oxoheptanoate → 4'-[(7-Butyl-5-oxo-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)methyl]biphenyl-2-carbonitrile

HRID 1688555Notes

Reaction equation

HRID 1688555 reaction equation
[NH:1]1[CH:5]=[N:4][C:3]([NH2:6])=[N:2]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:27](=O)[CH2:28][CH2:29][CH2:30][CH3:31])[C:23](OC)=[O:24])=[CH:17][CH:16]=1)#[N:8]>ClC1C=CC(Cl)=CC=1Cl>[CH2:28]([C:27]1[N:2]2[N:1]=[CH:5][N:4]=[C:3]2[NH:6][C:23](=[O:24])[C:22]=1[CH2:21][C:18]1[CH:17]=[CH:16][C:15]([C:10]2[C:9]([C:7]#[N:8])=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:20][CH:19]=1)[CH2:29][CH2:30][CH3:31]

Participants

4

Reactant 2

HCID 10807723Methyl 2-[(2'-cyanobiphenyl-4-yl)methyl]-3-oxoheptanoateHCID 178418311HCID 178418311, compound

Product 1

HCID 1357150474'-[(7-Butyl-5-oxo-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)methyl]biphenyl-2-carbonitrileYield 52.6%

Reagents, catalysts & solvents 1

HCID 131,2,4-TrichlorobenzeneSolvent

Procedure

A solution of 1H-1,2,4-triazol-3-amine (1.5 g) and methyl 2-[(2′-cyanobiphenyl-4-yl)methyl]-3-oxoheptanoate (7.1 g) in 1,2,4-trichlorobenzene (70 mL) was stirred at 190° C. for 6 hr. After evaporation of the solvent under reduced pressure, ethyl acetate was added to the obtained residue. The precipitated solid was collected by filtration to give the title compound as a colorless solid (3.6 g, 44%).

Workup

  1. customAfter evaporation of the solvent under reduced pressure, ethyl acetate
  2. additionwas added to the obtained residue
  3. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-655fb59d79dc4c49bb16443fcf1100d3
Source dataset
uspto-grants-2012_04
Patent number
US08148383B2

Reaction notes

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