Reaktion #466582

Reaktionsgleichung

N-(3,5-bis-trifluoromethyl-benzyl)-6-(4-cyanomethyl-piperazin-1-yl)-N-methyl-4-o-tolyl-nicotinamide

sodium azide

triethylammonium chloride

hydrochloric acid

→

title compound

Ausbeute 90.3%

N-(3,5-Bis-trifluoromethyl-benzyl)-N-methyl-6-[4-(1H-tetrazol-5-ylmethyl)-piperazin-1-yl]-4-o-tolyl-nicotinamide

Ausbeute 90.3%

Lösungsmittel

1-methyl-2-pyrrolidone

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturat reflux for 2 h
3. 3
   workup.ADDITIONwere added
4. 4
   Extraktionextracted with dichloromethane
5. 5
   TrocknenDrying of the combined extracts with sodium sulfate, concentration and flash column chromatography

Vorschrift

A mixture of 0.10 g (0.17 mmol) N-(3,5-bis-trifluoromethyl-benzyl)-6-(4-cyanomethyl-piperazin-1-yl)-N-methyl-4-o-tolyl-nicotinamide (Example 55), 34 mg (0.52 mmol) sodium azide and 36 mg (0.26 mmol) triethylammonium chloride in 1 ml 1-methyl-2-pyrrolidone was heated at reflux for 2 h. After cooling to room temperature 6 ml ice water were added. The mixture was acidified with 1N hydrochloric acid solution to pH 1-2 and extracted with dichloromethane. Drying of the combined extracts with sodium sulfate, concentration and flash column chromatography afforded 95 mg (88%) of the title compound as a light brown solid.

Quelle