Reaktion #170126

Reaktionsgleichung

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

3-(benzyloxy)azetidine hydrochloride

3-(Benzyloxy)azetidine hydrochloride

DIPEA

EDAC

→

title compound

Ausbeute 38.0%

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

Ausbeute 38.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenconcentrated to dryness
2. 2
   SonstigeThe residue was purified by precipitation in MeOH/H2O
3. 3
   Sonstigetriturated in acetone/diethyl ether

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 (60 mg, 0.24 mmol), DMF (5.8 mL), 3-(benzyloxy)azetidine hydrochloride (58 mg, 0.29 mmol; which may be prepared as described in Step 2), DIPEA (96 μL, 0.58 mmol), DMAP (2.4 mg, 0.02 mmol) and EDAC (56 mg, 0.29 mmol). The reaction mixture was stirred at room temperature overnight and concentrated to dryness. The residue was purified by precipitation in MeOH/H2O and then triturated in acetone/diethyl ether to give the title compound as a beige solid (33 mg, 38%).

Quelle