反应详情

2-methyl-1-(tetrahydropyran-4-yl)benzimidazole-5-carboxylic acid HCl salt (see Working Example 4-3) ((250 mg, 0.842 mmol), 2-amino-3-methoxyphenol (139 mg, 0.842 mmol), DMF (5 mL), and WSC (178 mg, 0.926 mmol) were stirred for 22 hours. Water was added and this was extracted with chloroform. After the organic layer obtained was dried over anhydrous sodium sulfate, it was filtered and concentrated. To a dioxane (5 mL) solution of the solid obtained was added methanesulfonic acid (283 mg, 2.95 mmol), and this was heated to reflux for 18 hours. After the reaction solution was cooled, water and saturated aqueous sodium hydrogen carbonate solution were added, and this was extracted with chloroform. After the organic layer obtained was dried over anhydrous sodium sulfate, it was filtered and concentrated. The residue obtained was purified by silica gel column chromatography to yield the title compound (10 mg, 3.3% yield) as brown crystals.

1. extractionthis was extracted with chloroform
2. customAfter the organic layer obtained
3. dry with materialwas dried over anhydrous sodium sulfate, it
4. filtrationwas filtered
5. concentrationconcentrated
6. customTo a dioxane (5 mL) solution of the solid obtained
7. temperaturethis was heated
8. temperatureto reflux for 18 hours
9. temperatureAfter the reaction solution was cooled
10. extractionthis was extracted with chloroform
11. customAfter the organic layer obtained
12. dry with materialwas dried over anhydrous sodium sulfate, it
13. filtrationwas filtered
14. concentrationconcentrated
15. customThe residue obtained
16. customwas purified by silica gel column chromatography