反应详情

A stream of nitrogen gas was bubbled through a stirred solution of 2-(3-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (3.68 g, 0.0128 mole), 1,1'-carbonyldiimidazole (2.07 g, 0.0128 mole), and anhydrous tetrahydrofuran (70 ml) for 21/2 hrs. at room temperature. A solution of N-methylpiperazine in 10 ml of tetrahydrofuran was added (rapid drop) and stirring was continued for 4 hrs. at room temperature. The tetrahydrofuran was evaporated and the residue was dissolved in methylene chloride (75 ml). The methylene chloride solution was washed with water (2×30 ml), dried over sodium sulfate, and concentrated in vacuo. The residue was converted to the sesquifumarate salt and crystallized from isopropyl alcohol-isopropyl ether. Recrystallization twice from isopropyl alcohol-isopropyl ether gave 3.2 g (46%) of a white solid, mp 190°-193° C. with decomposition.

1. customat room temperature
2. customat room temperature
3. customThe tetrahydrofuran was evaporated
4. dissolutionthe residue was dissolved in methylene chloride (75 ml)
5. washThe methylene chloride solution was washed with water (2×30 ml)
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated in vacuo
8. customcrystallized from isopropyl alcohol-isopropyl ether
9. customRecrystallization twice from isopropyl alcohol-isopropyl ether