N-ethyl-6-hydrazinyl-N-phenylpyridine-3-sulfonamide → 6-(4-benzyl-5-oxo-3-trifluoromethyl-2,5-dihydro-1H-pyrazol-1-yl)-N-ethyl-N-phenylpyridine-3-sulfonamide

HRID 45253Notes

Reaction equation

HRID 45253 reaction equation
[CH2:1]([CH:8]([C:13](O)(O)[C:14]([F:17])([F:16])[F:15])[C:9]([O:11]C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:20]([N:22]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[S:23]([C:26]1[CH:27]=[N:28][C:29]([NH:32][NH2:33])=[CH:30][CH:31]=1)(=[O:25])=[O:24])[CH3:21]>CO.C1(C)C=CC=CC=1.C(Cl)Cl>[CH2:1]([C:8]1[C:9](=[O:11])[N:32]([C:29]2[N:28]=[CH:27][C:26]([S:23]([N:22]([CH2:20][CH3:21])[C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)(=[O:25])=[O:24])=[CH:31][CH:30]=2)[NH:33][C:13]=1[C:14]([F:17])([F:16])[F:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 2095679N-ethyl-6-hydrazinyl-N-phenylpyridine-3-sulfonamideHCID 86659748Methyl 2-benzyl-4,4,4-trifluoro-3,3-dihydroxybutanoate

Product 1

HCID 674535166-(4-benzyl-5-oxo-3-trifluoromethyl-2,5-dihydro-1H-pyrazol-1-yl)-N-ethyl-N-phenylpyridine-3-sulfonamideYield 12.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 1 g (3.59 mmol) of methyl 2-benzyl-4,4,4-trifluoro-3,3-dihydroxybutanoate, 1.05 g (3.59 mmol) of N-ethyl-6-hydrazino-N-phenylpyridine-3-sulfonamide and 1 g of 4 Å molecular sieves in 8 mL of MeOH is heated for 12 hours at 90° C. At room temperature, the reaction medium is taken up in 30 mL of toluene, and refluxed for 12 hours in Dean-Stark apparatus. The reaction medium is then filtered and concentrated under reduced pressure, and the residue obtained is then taken up in 50 mL of DCM, washed with 1N HCl solution (2×50 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. The solid thus obtained is recrystallized from EtOH. 224 mg of 6-(4-benzyl-5-oxo-3-trifluoromethyl-2,5-dihydro-1H-pyrazol-1-yl)-N-ethyl-N-phenylpyridine-3-sulfonamide are obtained in the form of white crystals.

Workup

  1. customAt room temperature
  2. temperaturerefluxed for 12 hours in Dean-Stark apparatus
  3. filtrationThe reaction medium is then filtered
  4. concentrationconcentrated under reduced pressure
  5. customthe residue obtained
  6. washwashed with 1N HCl solution (2×50 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe solid thus obtained
  11. customis recrystallized from EtOH

Sources & evidence

ORD record
ord-930bb6d9a6a14313a4e7e06de0226f06
Source dataset
uspto-grants-2013_09
Patent number
US08541455B2

Reaction notes

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