Reaktion #1003448

Reaktionsgleichung

2-(2,4-bis-trifluoromethyl-benzylamino)-4-oxo-4,5-dihydro-imidazole-1-carboxylic acid benzyl ester

1,5-naphthyridine-6-carboxaldehyde

piperidine

→

2-(2,4-bis-trifluoromethyl-benzylamino)-5-[1,5]naphthyridin-2-ylmethylene-1,5-dihydro-imidazol-4-one

Ausbeute 23.2%

Lösungsmittel

iPrOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe suspension was then heated
2. 2
   Temperaturunder refluxing for 4.5 hrs
3. 3
   Sonstigeto give a suspension
4. 4
   Filtrationthe solid was collected by filtration
5. 5
   Waschenwashed with MeOH, ether
6. 6
   Sonstigedried in vacuum at 100° C. for 3 h

Vorschrift

To a mixture of 2-(2,4-bis-trifluoromethyl-benzylamino)-4-oxo-4,5-dihydro-imidazole-1-carboxylic acid benzyl ester (94.5 mg, 0.20 mmol), 1,5-naphthyridine-6-carboxaldehyde (31.7 mg, 0.20 mmol) and iPrOH (5.0 mL) in a 25-mL round bottom flask was added piperidine (0.05 mL) and the suspension was then heated under refluxing for 4.5 hrs to give a suspension. The reaction mixture was cooled to r.t. and the solid was collected by filtration, washed with MeOH, ether and dried in vacuum at 100° C. for 3 h to give 2-(2,4-bis-trifluoromethyl-benzylamino)-5-[1,5]naphthyridin-2-ylmethylene-1,5-dihydro-imidazol-4-one as a light yellow solid (21.6 mg, 23.2%). HR-ES (+) m/e calcd. for C21H13F6N5O: (M+H)+ 466.1097. Found: 466.1098.

Quelle