Reaktion #73502

Reaktionsgleichung

6-hydrazino-N,N-dimethylpyridine-3-sulfonamide

methyl 3-oxo-2-(pyridin-3-ylmethyl)butanoate

→

N,N-dimethyl-6-[3-methyl-5-oxo-4-(pyridin-3-ylmethyl)-2,5-dihydro-1H-pyrazol-1-yl]pyridine-3-sulfonamide

Ausbeute 28.0%

Lösungsmittel

EtOAc

EtOH AcOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenconcentrated under reduced pressure
2. 2
   SonstigeThe residue obtained
3. 3
   Waschenwashed successively with water (2×20 mL), saturated NaHCO3 solution (20 mL) and brine (20 mL)
4. 4
   Trocknendried over Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated under reduced pressure
7. 7
   Filtrationfiltered
8. 8
   Sonstigerecrystallized from a cyclohexane/EtOH mixture

Vorschrift

A mixture of 400 mg (1.85 mmol) of 6-hydrazino-N,N-dimethylpyridine-3-sulfonamide and 383 mg (1.85 mmol) of methyl 3-oxo-2-(pyridin-3-ylmethyl)butanoate in 4 mL of EtOH/AcOH mixture (1:1) is heated for 4 hours at 80° C. and then concentrated under reduced pressure. The residue obtained is taken up in 20 mL of EtOAc, washed successively with water (2×20 mL), saturated NaHCO3 solution (20 mL) and brine (20 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. The residue is then solidified in 20 mL of an Et2O/pentane mixture (1/1), filtered and recrystallized from a cyclohexane/EtOH mixture. 188 mg of N,N-dimethyl-6-[3-methyl-5-oxo-4-(pyridin-3-ylmethyl)-2,5-dihydro-1H-pyrazol-1-yl]pyridine-3-sulfonamide are obtained in the form of white crystals.

Quelle