Hydrochloric Acid → HCID 44159846, compound

Temperature

20 °C

To a suspension of ethyl 5-(2-aminopyridin-3-yl)isoxazol-3-carboxylate (381 mg, 1.63 mmol) in tetrahydrofuran (3.8 mL) and ethanol (3.8 mL) was added sodium borohydride (201 mg, 4.89 mmol) at 0° C. under a nitrogen atmosphere, which was stirred at 0° C. for one hour and at 20° C. for 21 hours. Under an ice water bath cooling, to the reaction mixture was added 2N hydrochloric acid (2.46 mL, 4.89 mmol) dropwise, which was stirred at 0° C. for 10 minutes and at room temperature for 30 minutes. Under the ice water bath cooling, after an aqueous solution of 5% sodium bicarbonate was added dropwise to adjust basic, the solution was extracted with ethyl acetate. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was evaporated under a reduced pressure. The residue was suspended in tetrahydrofuran (1.4 mL), to the reaction mixture was added sodium borohydride (67 mg, 1.63 mmol) at 0° C., which was washed thereto down with methanol (1.4 mL). After stirring at room temperature for one hour, the solution was stirred at 60° C. for five hours. Under an ice water bath cooling, to the reaction mixture was added 1N hydrochloric acid (1.63 mL, 1.63 mmol) dropwise, which was stirred at 0° C. for 10 minutes and at room temperature for 30 minutes. Under the ice water bath cooling, after adding 1N aqueous sodium hydroxide dropwise to adjust basic, the solution was extracted with ethyl acetate. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was evaporated under a reduced pressure to obtain the title compound (258 mg) as a pale yellow solid.

1. temperatureUnder an ice water bath cooling, to the reaction mixture
2. stirringwhich was stirred at 0° C. for 10 minutes and at room temperature for 30 minutes
3. extractionthe solution was extracted with ethyl acetate
4. dry with materialAfter the organic layer was dried over anhydrous magnesium sulfate
5. customthe solvent was evaporated under a reduced pressure
6. washwhich was washed
7. stirringAfter stirring at room temperature for one hour
8. stirringthe solution was stirred at 60° C. for five hours
9. temperatureUnder an ice water bath cooling, to the reaction mixture
10. stirringwhich was stirred at 0° C. for 10 minutes and at room temperature for 30 minutes
11. extractionthe solution was extracted with ethyl acetate
12. dry with materialAfter the organic layer was dried over anhydrous magnesium sulfate
13. customthe solvent was evaporated under a reduced pressure

ORD record

ord-55bba763b51f4282baf531296a32be5e

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08188119B2