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 2062395Notes

Reaction equation

HRID 2062395 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-0a779c96cf4743839abc7fca6ef6321e
Source dataset
uspto-grants-2012_10
Patent number
US08283353B2

Reaction notes

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