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 2048200Notes

Reaction equation

HRID 2048200 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-d98430585cfa42359faba9d98ecbf8ef
Source dataset
uspto-grants-2013_11
Patent number
US08592431B2

Reaction notes

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