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

HRID 519424Notes

Reaction equation

HRID 519424 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([NH2:7])=[N:5][N:6]=1.[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH:23]([C:29](=O)[CH2:30][CH2:31][CH3:32])[C:24](OCC)=[O:25])=[CH:18][CH:17]=1)#[N:9]>ClC1C=CC(Cl)=CC=1Cl>[CH3:1][C:2]1[N:3]=[C:4]2[NH:7][C:24](=[O:25])[C:23]([CH2:22][C:19]3[CH:20]=[CH:21][C:16]([C:11]4[C:10]([C:8]#[N:9])=[CH:15][CH:14]=[CH:13][CH:12]=4)=[CH:17][CH:18]=3)=[C:29]([CH2:30][CH2:31][CH3:32])[N:5]2[N:6]=1

Participants

4

Reactant 2

HCID 10020734Ethyl 2-[(2'-cyanobiphenyl-4-yl)methyl]-3-oxohexanoateHCID 178434112HCID 178434112, compound

Product 1

HCID 1360412724'-[(2-Methyl-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)methyl]biphenyl-2-carbonitrileYield 54.2%

Reagents, catalysts & solvents 1

HCID 131,2,4-TrichlorobenzeneSolvent

Procedure

A solution of 5-methyl-4H-1,2,4-triazol-3-amine (1.7 g) and ethyl 2-[(2′-cyanobiphenyl-4-yl)methyl]-3-oxohexanoate (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-70e2db3f6b9f41878e4539ab7481786a
Source dataset
uspto-grants-2015_08
Patent number
US09115136B2

Reaction notes

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