Reaktion #48040

Reaktionsgleichung

N-[(piperidin-1-yl)sulfonyl]-1-(4-chlorophenyl)-5-phenyl-4,5-dihydro-(1H)-pyrazole-3-carboxamide

PCl5

HCl

DIPEA

→

N-[(piperidin-1-yl)sulfonyl]-N′-methyl-1-(4-chlorophenyl)-5-phenyl-4,5-dihydro-(1H)-pyrazole-3-carboxamidine

Ausbeute 49.0%

Lösungsmittel

chlorobenzene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling the mixture to room temperature
2. 2
   Einengenfollowed by concentration in vacuo
3. 3
   workup.DISSOLUTIONthe residue is dissolved in dichloromethane
4. 4
   workup.STIRRINGThe resulting mixture is stirred for 1 hour at room temperature
5. 5
   Waschentwice washed with water
6. 6
   Trocknendried over MgSO4
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated in vacuo
9. 9
   SonstigeThe resulting residue is further purified by flash chromatography (silica gel, dichloromethane)
10. 10
    Sonstigefollowed by crystallization from diisopropyl ether

Vorschrift

Part B: A stirred mixture of N-[(piperidin-1-yl)sulfonyl]-1-(4-chlorophenyl)-5-phenyl-4,5-dihydro-(1H)-pyrazole-3-carboxamide (2.23 gram, 5 mmol), PCl5 (1.15 g, 5.5 mmol) and chlorobenzene (50 ml) is heated for 90 minutes at 140° C. After cooling the mixture to room temperature, followed by concentration in vacuo, the residue is dissolved in dichloromethane and methylamine.HCl (0.34 g, 5 mmol) and DIPEA (1.74 ml, 10 mmol) are successively added. The resulting mixture is stirred for 1 hour at room temperature, twice washed with water, dried over MgSO4, filtered and concentrated in vacuo. The resulting residue is further purified by flash chromatography (silica gel, dichloromethane), followed by crystallization from diisopropyl ether to give N-[(piperidin-1-yl)sulfonyl]-N′-methyl-1-(4-chlorophenyl)-5-phenyl-4,5-dihydro-(1H)-pyrazole-3-carboxamidine (1.12 gram, 49% yield). Melting point: 141-144° C. Rf (silica gel, diethyl ether=0.2).

Quelle