反应详情

To a solution of 2-benzamidoisonicotinic acid (0.50 g, 2.06 mmol) and 1,2-diaminopropane (0.35 mL, 4.12 mmol) in 1,4-dioxane (20 mL) was added phosphorus oxychloride (0.94 mL, 10.30 mmol) dropwise at ambient temperature under nitrogen atmosphere. The resulting solution was refluxed for 15 hours, cooled to ambient temperature and concentrated in vacuo to dryness. The residue was diluted with saturated aqueous sodium bicarbonate solution (50 mL), extracted with dichloromethane (4×50 mL), dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluting with ethyl acetate followed by 9:1:0.1 ratio of ethyl acetate, methanol and triethyl amine to give N-(4-(4-methyl-4,5-dihydro-1H-imidazol-2-yl)pyridin-2-yl)benzamide as a pale yellow foam (0.17 g, 29%): MS (ES+) m/z 281.5 (M+1).

1. temperatureThe resulting solution was refluxed for 15 hours
2. concentrationconcentrated in vacuo to dryness
3. additionThe residue was diluted with saturated aqueous sodium bicarbonate solution (50 mL)
4. extractionextracted with dichloromethane (4×50 mL)
5. dry with materialdried over anhydrous sodium sulphate
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe residue was purified by column chromatography
9. washeluting with ethyl acetate