Triethylamine → HCID 68525446, compound

A suspension of 4-[5-(4-cyanobenzoylamino)-pyridin-2-yloxy]benzoic acid (1.80 g, 5.01 mmol) in THF (20 mL) was cooled with ice-common salt, and to the solution was added triethylamine (0.77 mL, 5.51 mmol), and then ethyl chlorformate (0.53 mL, 5.51 mmol). The resulting solution was stirred at room temperature. Thirty minutes later, the reaction solution was filtered and insoluble matter was removed. The resulting filtrate was poured while stirring under ice cooling into an aqueous solution of sodium borohydride (0.95 g, 25.05 mmol) in 80% methanol (40 mL). After stirring for 30 minutes at room temperature, water (200 mL) was added to the reaction solution. The obtained mixture was extracted with ethyl acetate (200 mL). The ethyl acetate layer was washed with brine, dried over anhydrous sodium sulfate, and evaporated under reduced pressure. The residue was recrystallized from a mixed solution of ethyl acetate-n-hexane, to thereby yield 1.26 g of the title compound.

1. temperaturewas cooled with ice-common salt
2. filtrationThirty minutes later, the reaction solution was filtered
3. custominsoluble matter was removed
4. additionThe resulting filtrate was poured
5. stirringAfter stirring for 30 minutes at room temperature
6. extractionThe obtained mixture was extracted with ethyl acetate (200 mL)
7. washThe ethyl acetate layer was washed with brine
8. dry with materialdried over anhydrous sodium sulfate
9. customevaporated under reduced pressure
10. customThe residue was recrystallized from a mixed solution of ethyl acetate-n-hexane

ORD record

ord-f05650f142ca4bdda54d4b1adf17a61d

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08188277B2