تفاعل #170090

معادلة التفاعل

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

azetidine

HOBt

DIPEA

EDAC

6-bromo-3,4-dihydro-1,8-naphthyridin-2(1H)-one

→

title compound

المردود 62.0%

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

المردود 62.0%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   تركيزconcentrated to dryness
2. 2
   أخرىThe residue was purified twice on preparative TLC (eluent: dichloromethane/MeOH, 95/5)

الإجراء التجريبي

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), prepared (as in J. Med. Chem. 2003, 46, 9, 1627-1635) from 6-bromo-3,4-dihydro-1,8-naphthyridin-2(1H)-one described in U.S. Pat. No. 4,866,074 (Rorer Pharmaceutical Corp.), DMF (4.8 mL), HOBt (32 mg, 0.23 mmol), DIPEA (78 μL, 0.47 mmol), azetidine (16 μL, 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 twice on preparative TLC (eluent: dichloromethane/MeOH, 95/5) to give the title compound (31 mg, 62%) as a white solid.

المصدر