Réaction #170093

Équation de réaction

(2E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic acid hydrochloride

HOBt

DIPEA

4-piperidineethanol

EDAC

→

title compound

Rendement 55.0%

6-{(1E)-3-[4-(2-Hydroxyethyl)piperidin-1-yl]-3-oxoprop-1-en-1-yl}-3,4-dihydro-1,8-naphthyridin-2(1H)-one

Rendement 55.0%

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   Concentrationconcentrated to dryness
2. 2
   AutreThe residue was purified on column chromatography (eluent: dichloromethane/MeOH, 95/5)
3. 3
   Autreto give a white solid
4. 4
   AutreThis solid was triturated in MeOH
5. 5
   Filtrationfiltered
6. 6
   Lavagewashed with MeOH and diethyl ether
7. 7
   Autredried

Mode opératoire

A 16 mL vial flask was successively charged with (2E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic acid hydrochloride (50 mg, 0.20 mmol), DMF (4.8 mL), HOBt (32 mg, 0.23 mmol), DIPEA (78 μL, 0.47 mmol), 4-piperidineethanol (30 mg, 0.23 mmol) and EDAC (45 mg, 0.23 mmol). The reaction mixture was stirred at room temperature overnight and concentrated to dryness. The residue was purified on column chromatography (eluent: dichloromethane/MeOH, 95/5) to give a white solid. This solid was triturated in MeOH, filtered, washed with MeOH and diethyl ether and dried to give the title compound (35 mg, 55%) as a white solid.

Source