1-Bromo-3-chloropropane → 5-Amino-4-[3-(3-chloropropylamino)benzoyl]-1-(4-fluorophenyl)pyrazole

HRID 429374Notes

Reaction equation

HRID 429374 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:14](=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH2:21])[CH:16]=1.Br[CH2:24][CH2:25][CH2:26][Cl:27].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C(OCC)(=O)C>[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:14](=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][CH2:24][CH2:25][CH2:26][Cl:27])[CH:16]=1

Participants

6

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 10796Cesium carbonateHCID 222628105-Amino4-(3-aminobenzoyl)-1-(4-fluorophenyl)pyrazole

Product 1

HCID 222628035-Amino-4-[3-(3-chloropropylamino)benzoyl]-1-(4-fluorophenyl)pyrazoleYield 33.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-amino-4-(3-aminobenzoyl)-1-(4-fluorophenyl)pyrazole (0.5 g, 1.6 mmol), 1-bromo-3-chloropropane (0.26 g, 1.6 mmol) and cesium carbonate (0.52 g, 1.6 mmol) in dimethylformamide (25 ml) was heated at 80° C. After 2 days, the reaction mixture was cooled to room temperature and diluted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography (elution gradient: 20% acetone/hexanes) to give 5-amino-4-[3-(3-chloropropylamino)benzoyl]-1-(4-fluorophenyl)pyrazole (0.2 g) as a solid.

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash chromatography (elution gradient: 20% acetone/hexanes)

Sources & evidence

ORD record
ord-9566262071704cd5bb3bf67d3d3ebe85
Source dataset
uspto-grants-2001_11
Patent number
US06316466B1

Reaction notes

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