Chloroform → HCID 66872382, compound

2-Amino-3-methoxypyridine (1.50 g) was dissolved in THF (20 mL), and at 0° C., triethylamine (3.37 mL) and 3-iodobenzoyl chloride (3.23 g) were added thereto and stirred at room temperature for 30 minutes. Triethylamine (3.37 mL) and 3-iodobenzoyl chloride (3.23 g) were further added and stirred at room temperature for 18 hours. Chloroform was added to the reaction liquid, then washed with aqueous saturated sodium hydrogencarbonate solution, and dried with sodium sulfate. The drying agent was removed through filtration, and the solvent was evaporated off under reduced pressure. The residue was suspended in ethyl acetate (about 50 mL) added thereto, then the solid was collected through filtration as a colorless solid (5.96 g). Methanol (50 mL) and aqueous 2 M sodium hydrogencarbonate solution (3.42 mL) were added to the obtained solid (2.00 g), and stirred at room temperature for 18 hours. Methanol was evaporated off under reduced pressure, then ethyl acetate was added to the residue, washed with water and saturated brine in that order, and dried with sodium sulfate. The drying agent was removed through filtration, and the solvent was evaporated off under reduced pressure. The residue was purified through silica gel column chromatography (ethyl acetate/hexane=from 0% to 100%, gradient) to give the entitled compound (1.15 g, 80%) as an orange oil.

1. stirringstirred at room temperature for 18 hours
2. washwashed with aqueous saturated sodium hydrogencarbonate solution
3. dry with materialdried with sodium sulfate
4. customThe drying agent was removed through filtration
5. customthe solvent was evaporated off under reduced pressure
6. additionadded
7. customthe solid was collected through
8. filtrationfiltration as a colorless solid (5.96 g)
9. additionMethanol (50 mL) and aqueous 2 M sodium hydrogencarbonate solution (3.42 mL) were added to the obtained solid (2.00 g)
10. stirringstirred at room temperature for 18 hours
11. customMethanol was evaporated off under reduced pressure
12. additionethyl acetate was added to the residue
13. washwashed with water and saturated brine in that order
14. dry with materialdried with sodium sulfate
15. customThe drying agent was removed through filtration
16. customthe solvent was evaporated off under reduced pressure
17. customThe residue was purified through silica gel column chromatography (ethyl acetate/hexane=from 0% to 100%, gradient)

ORD record

ord-fb710131b3974de189256f164bee0dfe

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08420823B2