Sodium Iodide → 3-({[4-({Cyclohexyl[5-(5-fluoropyridin-2-yl)-2-methylfuran-3-yl]methyl}amino)phenyl]carbonyl}amino)propanoic acid

온도

80 °C

A mixture of 2-{4-[chloro(cyclohexyl)methyl]-5-methylfuran-2-yl}-5-fluoropyridine (0.4 g), ethyl 3-{[(4-aminophenyl)carbonyl]amino}propanoate (0.3 g), sodium carbonate (0.2 g) and sodium iodide (0.2 g) in N,N-dimethylacetamide (10 mL) was stirred overnight at 80° C. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (20% ethyl acetate/hexane to 50% ethyl acetate/hexane). To the residue were added ethanol (2 mL), tetrahydrofuran (2 mL) and 1N lithium hydroxide (1.2 mL), and the mixture was stirred at room temperature for 1 hr. The solvent was evaporated under reduced pressure, and water (10 mL) was added. The mixture was neutralized with 1N hydrochloric acid under ice-cooling, and stirred for 1 hr. The resulting precipitate was collected by filtration and dried to give the title compound (285 mg, 52%).

1. extractionthe mixture was extracted with ethyl acetate
2. washThe organic layer was washed with saturated brine
3. dry with materialdried over magnesium sulfate
4. customThe solvent was evaporated under reduced pressure
5. customthe residue was purified by silica gel chromatography (20% ethyl acetate/hexane to 50% ethyl acetate/hexane)
6. additionTo the residue were added ethanol (2 mL), tetrahydrofuran (2 mL) and 1N lithium hydroxide (1.2 mL)
7. stirringthe mixture was stirred at room temperature for 1 hr
8. customThe solvent was evaporated under reduced pressure, and water (10 mL)
9. additionwas added
10. temperaturecooling
11. stirringstirred for 1 hr
12. filtrationThe resulting precipitate was collected by filtration
13. customdried

ORD 기록

ord-e09a388a65184e2f95329f5dc2a973c0

출처 데이터셋

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08309580B2