反応 #170136

反応方程式

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

2-[(azetidin-3-yloxy)methyl]-1,3-thiazole hydrochloride

2-[(Azetidin-3-yloxy)methyl]-1,3-thiazole hydrochloride

DIPEA

EDAC

→

title compound

収率 24.0%

6-{(1E)-3-Oxo-3-[3-(1,3-thiazol-2-ylmethoxy)azetidin-1-yl]prop-1-en-1-yl}-3,4-dihydro-1,8-naphthyridin-2(1H)-one

収率 24.0%

溶媒

DMF

反応条件

後処理

1. 1
   濃縮concentrated to dryness
2. 2
   その他The residue was precipitated in methanol/water
3. 3
   ろ過filtered
4. 4
   その他The resulting solid was purified on column chromatography (eluent: 96/4 dichloromethane/MeOH)
5. 5
   その他then triturated in pentane

実験手順

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), 2-[(azetidin-3-yloxy)methyl]-1,3-thiazole hydrochloride (99 mg, 0.48 mmol; which may be prepared as described in Step 3), DIPEA (119 μL, 0.72 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 precipitated in methanol/water and then filtered. The resulting solid was purified on column chromatography (eluent: 96/4 dichloromethane/MeOH) then triturated in pentane and MeOH to give the title compound (21 mg, 24%) as a white solid.

出典