Reaktion #170218

Reaktionsgleichung

3-(3,3,3-Trifluoropropoxy)azetidine hydrochloride

EDCI

HOBt

diisopropylethylamine

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

→

title product

Ausbeute 39.0%

(E)-6-(3-Oxo-3-(3-(3,3,3-trifluoropropoxy)azetidin-1-yl)prop-1-enyl)-3,4-dihydro-1,8-naphthyridin-2(1H)-one

Ausbeute 39.0%

Lösungsmittel

water

ethyl acetate

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe aqueous layer was separated
2. 2
   Extraktionextracted with ethyl acetate (2×30 mL)
3. 3
   WaschenThe combined organic phases were washed with a saturated solution of sodium chloride (3×30 mL)
4. 4
   Trocknendried over sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated to dryness
7. 7
   SonstigeThe residue was purified by chromatography on silica gel
8. 8
   SonstigeThe residue was finally precipitated from methanol

Vorschrift

3-(3,3,3-Trifluoropropoxy)azetidine hydrochloride (194 mg, 0.94 mmol), EDCI (181 mg, 0.94 mmol), HOBt (128 mg, 0.94 mmol) and diisopropylethylamine (274 μL, 1.57 mmol) were successively added to a solution of (E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)-acrylic acid hydrochloride (160 mg, 0.63 mmol) in dimethylformamide (15 mL) at room temperature. The reaction mixture was stirred overnight then diluted by addition of ethyl acetate (30 mL) and water (40 mL). The aqueous layer was separated and extracted with ethyl acetate (2×30 mL). The combined organic phases were washed with a saturated solution of sodium chloride (3×30 mL), dried over sodium sulfate, filtered and concentrated to dryness. The residue was purified by chromatography on silica gel using dichloromethane/methanol (98:2) as eluent. The residue was finally precipitated from methanol to afford the title product as a white solid (90 mg, 39%).

Quelle