Reaktion #1055905

Reaktionsgleichung

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

6-formyl-4-isopropoxy-[1,5]naphthyridine-3-carbonitrile

piperidine

→

4-isopropoxy-6-[5-oxo-2-(2-trifluoromethyl-benzylamino)-3,5-dihydro-imidazol-4-ylidenemethyl]-[1,5]naphthyridine-3-carbonitrile

Lösungsmittel

iPrOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe suspension was then heated
2. 2
   Temperaturunder refluxing for 5 h
3. 3
   Sonstigeto give a brown solution
4. 4
   Einengenconcentrated
5. 5
   Sonstigeto give a light yellow solid, 66.3 mg, which
6. 6
   Sonstigewas purified by flash column purification

Vorschrift

To a mixture of 4-oxo-2-(2-trifluoromethyl-benzylamino)-4,5-dihydro-imidazole-1-carboxylic acid benzyl ester (70.4 mg, 0.18 mmol) (prepared as described in C-H Kwon et al. J. Med. Chem. 1991, 34, 1845-1849), 6-formyl-4-isopropoxy-[1,5]naphthyridine-3-carbonitrile (56.5 mg, 0.23 mmol) (see Example 1) and iPrOH (5 mL) in a 25-mL round bottom flask was added piperidine (0.05 mL) and the suspension was then heated under refluxing for 5 h to give a brown solution. The reaction mixture was cooled to r.t. and concentrated to give a light yellow solid, 66.3 mg, which was purified by flash column purification to give 4-isopropoxy-6-[5-oxo-2-(2-trifluoromethyl-benzylamino)-3,5-dihydro-imidazol-4-ylidenemethyl]-[1,5]naphthyridine-3-carbonitrile, as a light yellow solid, 18.6 mg (21.5%). HR-ES (+) m/e calcd for C24H19F3N6O2 (M+H)+ 481.1595. found 481.1595.

Quelle