反应详情

To a stirred suspension of 2-aminomethyl-3-chloropyrazine hydrochloride (content 77%; 4.34 mmol, 0.81 g) in dichloromethane (150 ml) were added 3-methyl-3-oxetanecarboxylic acid (4.34 mmol, 0.504 g), triethylamine (9.56 mmol, 1.33 ml), 4-dimethylaminopyridine (0.434 mmol, 0.053 g) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (8.69 mmol, 1.67 g). After stirring for 16 hours at room temperature the suspension was filtered over decalite and the decalite was washed with dichloromethane. The combined filtrates were washed with 0.3 N hydrochloric acid (350 mL), 0.03 N hydrochloric acid (350 mL) and sodium hydrogencarbonate (aq). All aqueous layers were twice extracted with dichloromethane. The combined organic extracts were dried (sodium sulfate) and concentrated in vacuo to give crude material. Solid sodium chloride was added to all aqueous layers and these were extracted five times with dichloromethane. The combined organic extracts were dried (sodium sulfate) and concentrated in vacuo to give a second crop of crude material. The combined crude products were purified using chromatography (silica gel, ethyl acetate) to yield N-((3-chloropyrazin-2-yl)methyl)-3-methyloxetane-3-carboxamide (0.58 g).

1. filtrationwas filtered over decalite
2. washthe decalite was washed with dichloromethane
3. washThe combined filtrates were washed with 0.3 N hydrochloric acid (350 mL), 0.03 N hydrochloric acid (350 mL) and sodium hydrogencarbonate (aq)
4. extractionAll aqueous layers were twice extracted with dichloromethane
5. dry with materialThe combined organic extracts were dried (sodium sulfate)
6. concentrationconcentrated in vacuo
7. customto give crude material
8. extractionthese were extracted five times with dichloromethane
9. dry with materialThe combined organic extracts were dried (sodium sulfate)
10. concentrationconcentrated in vacuo
11. customto give a second crop of crude material
12. customwere purified