Triethylamine → HCID 46947566, compound

HRID 1946363Notes

Reaction equation

HRID 1946363 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][N:10]1[CH:14]=[CH:13][C:12]([NH2:15])=[N:11]1.C(N(CC)CC)C.[F:23][C:24]1[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[C:25]=1[C:26](Cl)=[O:27]>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][N:10]1[CH:14]=[CH:13][C:12]([NH:15][C:26](=[O:27])[C:25]2[C:24]([F:23])=[CH:32][CH:31]=[CH:30][C:29]=2[F:33])=[N:11]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 874382,6-Difluorobenzoyl chlorideHCID 53027431-((2,4-Dichlorophenyl)methyl)-1H-pyrazol-3-amine

Product 1

HCID 46947566HCID 46947566, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-[(2,4-Dichlorophenyl)methyl]-1H-pyrazol-3-amine (40 μl, 0.23 mmol, Art-Chem GmbH) was dissolved in dichloromethane (2 ml). Triethylamine (64 μl, 0.46 mmol) and then 2,6-difluorobenzoyl chloride (49 mg, 0.28 mmol, Aldrich) were added and the reaction was stirred at room temperature for 2 h. The reaction was quenched by addition of water (5 ml). The organic phase was separated (by hydrophobic frit) and concentrated under a flow of nitrogen. The residue was purified by MDAP (supelcosil ABZ+Plus column) eluting with solvents A/B (A: Water+0.1% Formic acid, B: MeCN:Water 95:5+0.05% Formic acid) (Method A). The appropriate fractions were concentrated in vacuo then under nitrogen flow. The sample was dissolved in methanol and applied to a 5 g aminopropyl ion exchange cartridge (prewashed with MeOH) and eluted with MeOH. The relevant fractions were combined and concentrated to give the title compound as a colourless solid (36 mg); LCMS: (System 1) MH+=382/384, tRET=3.47 min.

Workup

  1. customThe reaction was quenched by addition of water (5 ml)
  2. customThe organic phase was separated (by hydrophobic frit)
  3. concentrationconcentrated under a flow of nitrogen
  4. customThe residue was purified by MDAP (supelcosil ABZ+Plus column)
  5. washeluting with solvents A/B (A: Water+0.1% Formic acid, B
  6. concentrationThe appropriate fractions were concentrated in vacuo
  7. dissolutionThe sample was dissolved in methanol
  8. washeluted with MeOH
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-9c8fb67c29484be08d79ab111555cd5a
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

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