Triethylamine → HCID 69426394, compound

HRID 916700Notes

Reaction equation

HRID 916700 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10](=O)[CH2:11][C:12]([C:14]2[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=2)[C:17]#[N:18])=O)=[CH:4][CH:3]=1.C(O)(=O)C(O)=O.[CH2:29]([NH:31][NH2:32])[CH3:30].CCN(CC)CC>CCO>[CH2:29]([N:31]1[C:10]([CH2:9][CH2:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:11][C:12]([C:14]2[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=2)[C:17]#[N:18])=[N:32]1)[CH3:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 96181Hydrazine, ethyl-, ethanedioate (1:1)HCID 69426286HCID 69426286, compound

Product 1

HCID 69426394HCID 69426394, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-[5-(4-fluorophenyl)-3-oxo-pentanoyl]-benzonitrile (1.0 g, 3.39 mmol), ethyl hydrazine oxalate (763 mg, 5.08 mmol) and Et3N (709 □L, 5.08 mmol) in EtOH (50 mL) was heated at reflux for 3 hours. The solvent was removed under reduced pressure and the residue was partitioned between EtOAc (100 mL) and H2O (50 mL). The organics were separated, washed with brine (50 mL), concentrated under reduced pressure, and the residue purified by column chromatography on silica eluting with 40% EtOAc/iso-hexanes to yield first 3-{1-ethyl-5-[2-(4-fluorophenyl)-ethyl]-1H-pyrazol-3-yl}-benzonitrile (280 mg, 26%) (by-product) and then 3-{1-ethyl-3-[2-(4-fluorophenyl)-ethyl]-1H-pyrazol-5-yl}-benzonitrile (380 mg, 35%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was partitioned between EtOAc (100 mL) and H2O (50 mL)
  5. customThe organics were separated
  6. washwashed with brine (50 mL)
  7. concentrationconcentrated under reduced pressure
  8. customthe residue purified by column chromatography on silica eluting with 40% EtOAc/iso-hexanes

Sources & evidence

ORD record
ord-3625ac737f014d938f6147fe424b44cb
Source dataset
uspto-grants-2007_09
Patent number
US07271191B2

Reaction notes

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