Methyl 4-aminobenzoate → Methyl 4-{[cyclohexyl(3-methylfuro[3,2-b]pyridin-2-yl)methyl]amino}benzoate

To a mixture of cyclohexyl(3-methylfuro[3,2-b]pyridin-2-yl)methanone (1.08 g) synthesized above, methyl 4-aminobenzoate (738 mg), triethylamine (4.95 mL) and methylene chloride (20 mL) was added titanium (IV) chloride (584 μL), and the mixture was stirred under argon atmosphere overnight at room temperature. Saturated aqueous sodium hydrogen carbonate solution was added to quench the reaction, and the reaction mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to give a dark brown oil. To a solution (20 mL) of the obtained oil in tetrahydrofuran were added acetic acid (1.27 mL) and sodium cyanoborohydride (558 mg), and the mixture was stirred at room temperature for 1 hr. Saturated aqueous sodium hydrogen carbonate solution was added to quench the reaction, tetrahydrofuran was evaporated in an evaporator, and the residue was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (50% ethyl acetate/hexane) to give the title object compound (789 mg, 47%) as a pale-brown solid.

1. customto quench
2. customthe reaction
3. extractionthe reaction mixture was extracted with ethyl acetate
4. washThe extract was washed with saturated brine
5. dry with materialdried over magnesium sulfate
6. concentrationconcentrated under reduced pressure
7. customto give a dark brown oil
8. stirringthe mixture was stirred at room temperature for 1 hr
9. customto quench
10. customthe reaction, tetrahydrofuran
11. customwas evaporated in an evaporator
12. extractionthe residue was extracted with ethyl acetate
13. washThe extract was washed with saturated brine
14. dry with materialdried over magnesium sulfate
15. concentrationconcentrated under reduced pressure
16. customThe residue was purified by silica gel column chromatography (50% ethyl acetate/hexane)

ORD-Eintrag

ord-0aaee667654d48ed995d43cb5404e86f

Quelldatensatz

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08436043B2