N-ethyl-6-hydrazinyl-N-phenylpyridine-3-sulfonamide → N-ethyl-6-[3-methyl-4-(1-methyl-1-phenylethyl)-5-oxo-2,5-dihydro-1H-pyrazol-1-yl]-N-phenylpyridine-3-sulfonamide

HRID 45220Notes

Reaction equation

HRID 45220 reaction equation
[C:1]([CH:4]([C:9]([CH3:17])([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:10])[C:5]([O:7]C)=O)(=O)[CH3:2].[CH2:18]([N:20]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[S:21]([C:24]1[CH:25]=[N:26][C:27]([NH:30][NH2:31])=[CH:28][CH:29]=1)(=[O:23])=[O:22])[CH3:19]>CCO.CC(O)=O.CCCCC>[CH2:18]([N:20]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[S:21]([C:24]1[CH:25]=[N:26][C:27]([N:30]2[C:5](=[O:7])[C:4]([C:9]([CH3:17])([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH3:10])=[C:1]([CH3:2])[NH:31]2)=[CH:28][CH:29]=1)(=[O:23])=[O:22])[CH3:19]

Participants

5

Reactant 2

HCID 2095679N-ethyl-6-hydrazinyl-N-phenylpyridine-3-sulfonamideHCID 86659735Methyl 2-acetyl-3-methyl-3-phenylbutanoate

Product 1

HCID 46701955N-ethyl-6-[3-methyl-4-(1-methyl-1-phenylethyl)-5-oxo-2,5-dihydro-1H-pyrazol-1-yl]-N-phenylpyridine-3-sulfonamideYield 44%

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 18476134Acetic acid ethanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 200 mg (0.85 mmol) of methyl 2-acetyl-3-methyl-3-phenylbutanoate in 2 mL of EtOH/AcOH mixture (1:1) are added 249 mg (0.85 mmol) of N-ethyl-6-hydrazino-N-phenylpyridine-3-sulfonamide and the reaction mixture is then heated for 2 hours at 90° C. After concentrating under reduced pressure, the residue is taken up in 100 mL of DCM, washed with 2×30 mL of saturated NaHCO3 solution, dried over Na2SO4, filtered, concentrated under reduced pressure and then purified by chromatography on a column of silica gel, eluting with a cyclohexane/EtOAc gradient of 0 to 20% EtOAc. After concentrating under reduced pressure, 312 mg of a yellow oil are obtained, and are solidified in 20 mL of pentane. The solid obtained is filtered off, and then dried under vacuum. 178 mg of N-ethyl-6-[3-methyl-4-(1-methyl-1-phenylethyl)-5-oxo-2,5-dihydro-1H-pyrazol-1-yl]-N-phenylpyridine-3-sulfonamide are obtained in the form of a white powder.

Workup

  1. concentrationAfter concentrating under reduced pressure
  2. washwashed with 2×30 mL of saturated NaHCO3 solution
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. custompurified by chromatography on a column of silica gel
  7. washeluting with a cyclohexane/EtOAc gradient of 0 to 20% EtOAc
  8. concentrationAfter concentrating under reduced pressure, 312 mg of a yellow oil
  9. customare obtained
  10. customThe solid obtained
  11. filtrationis filtered off
  12. customdried under vacuum

Sources & evidence

ORD record
ord-2d0e8aff785943749324b2dccdf7ac01
Source dataset
uspto-grants-2013_09
Patent number
US08541455B2

Reaction notes

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