反应详情

To 5-(benzoxazol-2-yl)-2-hydroxymethyl-1-(tetrahydropyran-4-yl)benzimidazole (see Working Example 13-2) (168 mg, 0.481 mmol) was added thionyl chloride (1.5 mL), and this was heated to reflux with stirring for 2 hours. After the reaction was complete, this was cooled to room temperature and concentrated. The crystals obtained were suspended in tetrahydrofuran, and to this was added sodium iodide (108 mg, 0.722 mmol) and benzylamine (258 mg, 2.41 mmol), and this was heated to reflux with stirring for 1.5 hours. After the reaction was complete, this was cooled to room temperature, water was added, and this was extracted with ethyl acetate. The organic layer obtained was dried over anhydrous sodium sulfate, filtered, and concentrated to give an residue that was purified by silica gel column chromatography to yield the title compound (182 mg, 86% yield) as a colorless amorphous mass.

1. temperaturethis was heated
2. temperatureto reflux
3. concentrationconcentrated
4. customThe crystals obtained
5. temperaturethis was heated
6. temperatureto reflux
7. stirringwith stirring for 1.5 hours
8. temperaturethis was cooled to room temperature
9. extractionthis was extracted with ethyl acetate
10. customThe organic layer obtained
11. dry with materialwas dried over anhydrous sodium sulfate
12. filtrationfiltered
13. concentrationconcentrated
14. customto give an residue that
15. customwas purified by silica gel column chromatography