Trifluoroacetic acid → N-((2S)-1-((2-(4-hydroxyphenyl)[1,3]thiazolo[4,5-c]pyridin-6-yl)oxy)propan-2-yl)acetamide

A mixture of 2-ethylhexyl 3-((2-(((2S)-2-acetamidopropyl)oxy)-5-((4-(cyclopropylmethoxy)benzoyl)amino)pyridin-4-yl)sulfanyl)propanoate (740 mg), sodium ethoxide (20% ethanol solution, 840 mg) and THF (10 mL) was stirred at room temperature for 30 min. The reaction mixture was cooled to 0° C., trifluoroacetic acid (0.475 mL) was added thereto, the obtained mixture was stirred at 70° C. for 1 hr. The reaction mixture was cooled to 0° C., and the precipitate was collected by filtration, and washed with diisopropyl ether. The obtained residue was dissolved in trifluoroacetic acid (5 mL), and the obtained solution was stirred at 70° C. for 1 hr. The reaction mixture was added to saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The combined organic layer were washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (379 mg).

1. temperatureThe reaction mixture was cooled to 0° C.
2. stirringthe obtained mixture was stirred at 70° C. for 1 hr
3. temperatureThe reaction mixture was cooled to 0° C.
4. filtrationthe precipitate was collected by filtration
5. washwashed with diisopropyl ether
6. dissolutionThe obtained residue was dissolved in trifluoroacetic acid (5 mL)
7. stirringthe obtained solution was stirred at 70° C. for 1 hr
8. additionThe reaction mixture was added to saturated aqueous sodium hydrogen carbonate solution
9. extractionthe mixture was extracted with ethyl acetate
10. washThe combined organic layer were washed with saturated brine
11. dry with materialdried over anhydrous magnesium sulfate
12. customthe solvent was evaporated under reduced pressure

ORD record

ord-02ba7f13f7f9410786ca549879cf5fe7

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09133129B2