Pyridine → HCID 178522275, compound

HRID 719294Notes

Reaction equation

HRID 719294 reaction equation
[NH2:1][C:2]1[C:3]([C:13]([F:16])([F:15])[F:14])=[N:4][NH:5][C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.N1C=CC=CC=1.[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>ClCCl>[C:7]1([C:6]2[NH:5][N:4]=[C:3]([C:13]([F:16])([F:15])[F:14])[C:2]=2[NH:1][C:23](=[O:30])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 178507812HCID 178507812, compound

Product 1

HCID 178522275HCID 178522275, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.0 g of 4-amino-5-phenyl-3-trifluoromethyl-1H-pyrazole in 30 mL of dichloromethane was treated with 1.1 mL of pyridine followed by 0.57 mL of benzoyl chloride. The reaction mixture was stirred at RT for 5 hours and then concentrated. The residue was partitioned between ethyl acetate and water. The organic portion was washed with brine, dried over magnesium sulfate, filtered and concentrated. The residue was purified by MPLC, eluting with 2/3 ethyl acetate/heptane, to give the title compound as a white solid, melting point 229–230° C.

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between ethyl acetate and water
  3. washThe organic portion was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by MPLC
  8. washeluting with 2/3 ethyl acetate/heptane

Sources & evidence

ORD record
ord-21a22705615b4fc2ab0001d7dd76f769
Source dataset
uspto-grants-2006_11
Patent number
US07132428B2

Reaction notes

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