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

HRID 1412175Notes

Reaction equation

HRID 1412175 reaction equation
C[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])=[C:18]([F:34])[CH:17]=1)#[N:9]>ClC1C=CC(Cl)=CC=1Cl>[F:34][C:18]1[CH:17]=[C:16]([C:11]2[C:10]([C:8]#[N:9])=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:21]=[CH:20][C:19]=1[CH2:22][C:23]1[C:24](=[O:25])[NH:7][C:4]2[N:5]([N:6]=[CH:2][N:3]=2)[C:29]=1[CH2:30][CH2:31][CH3:32]

Participants

4

Reactant 2

HCID 57460949Ethyl 2-[(2'-cyano-3-fluorobiphenyl-4-yl)methyl]-3-oxohexanoateHCID 178434112HCID 178434112, compound

Product 1

HCID 1363371393'-Fluoro-4'-[(5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)methyl]biphenyl-2-carbonitrileYield 44.8%

Reagents, catalysts & solvents 1

HCID 131,2,4-TrichlorobenzeneSolvent

Procedure

A solution of 5-methyl-4H-1,2,4-triazol-3-amine (8.9 g) and ethyl 2-[(2′-cyano-3-fluorobiphenyl-4-yl)methyl]-3-oxohexanoate (25 g) in 1,2,4-trichlorobenzene (120 mL) was stirred at 180° C. for 16 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 (11.8 g, 43%).

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-fdb412c0dd7245edb740fa82e9201c84
Source dataset
uspto-grants-2014_12
Patent number
US08921379B2

Reaction notes

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