반응 #170106

반응 방정식

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

3-phenoxypyrrolidine hydrochloride

3-Phenoxypyrrolidine hydrochloride

DIPEA

EDAC

→

title compound

수율 68.8%

6-[(1E)-3-Oxo-3-(3-phenoxypyrrolidin-1-yl)prop-1-en-1-yl]-3,4-dihydro-1,8-naphthyridin-2(1H)-one

수율 68.8%

용매

DMF

반응 조건

후처리

1. 1
   농축concentrated to dryness
2. 2
   기타The residue was purified on preparative TLC (eluent: dichloromethane/NH3 7N in MeOH, 2.5%)
3. 3
   기타to give a pale yellow solid
4. 4
   기타This solid was triturated in methanol
5. 5
   여과filtered
6. 6
   세척washed with methanol, acetone and diethyl ether
7. 7
   기타then dried

실험 절차

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 (30 mg, 0.12 mmol), DMF (3 mL), 3-phenoxypyrrolidine hydrochloride (28 mg, 0.14 mmol; which may be prepared as described in Step 3), DIPEA (48 μL, 0.28 mmol) and EDAC (27 mg, 0.14 mmol). The reaction mixture was stirred at room temperature overnight and concentrated to dryness. The residue was purified on preparative TLC (eluent: dichloromethane/NH3 7N in MeOH, 2.5%) to give a pale yellow solid. This solid was triturated in methanol, filtered, washed with methanol, acetone and diethyl ether then dried to give the title compound (30 mg, 68%) as a white solid.

출처