Reaktion #170093

Reaktionsgleichung

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

HOBt

DIPEA

4-piperidineethanol

EDAC

→

title compound

Ausbeute 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

Ausbeute 55.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenconcentrated to dryness
2. 2
   SonstigeThe residue was purified on column chromatography (eluent: dichloromethane/MeOH, 95/5)
3. 3
   Sonstigeto give a white solid
4. 4
   SonstigeThis solid was triturated in MeOH
5. 5
   Filtrationfiltered
6. 6
   Waschenwashed with MeOH and diethyl ether
7. 7
   Sonstigedried

Vorschrift

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.

Quelle