Triethylamine → HCID 71147160, compound

To a mixture of 3-amino-5-bromothiophene-2-carboxamide (221 mg) produced in Example 1, step D, triethylamine (0.153 mL) and tetrahydrofuran (5.0 mL) was added chloro(phenyl)acetylchloride (0.174 mL) with stirring at room temperature. The reaction mixture was stirred for 10 min, and pyrrolidine (0.42 mL) was added. The reaction mixture was stirred with heating at 70° C. for 1 hr, and the reaction system was concentrated under reduced pressure. To the residue was added 2M aqueous sodium hydroxide solution (1.5 mL), and the mixture was stirred with heating at 120° C. for 2 hr. The mixture was extracted with ethyl acetate and dried over anhydrous sodium sulfate. Insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate/hexane). The obtained yellow solid was washed with ethyl acetate (2 mL) to give the title compound (330 mg) as a yellow solid.

1. stirringThe reaction mixture was stirred for 10 min
2. stirringThe reaction mixture was stirred
3. temperaturewith heating at 70° C. for 1 hr
4. concentrationthe reaction system was concentrated under reduced pressure
5. additionTo the residue was added 2M aqueous sodium hydroxide solution (1.5 mL)
6. stirringthe mixture was stirred
7. temperaturewith heating at 120° C. for 2 hr
8. extractionThe mixture was extracted with ethyl acetate
9. dry with materialdried over anhydrous sodium sulfate
10. customInsoluble material was removed by filtration
11. concentrationthe filtrate was concentrated under reduced pressure
12. customThe residue was purified by basic silica gel column chromatography (ethyl acetate/hexane)
13. washThe obtained yellow solid was washed with ethyl acetate (2 mL)

ORD record

ord-1293564f8f51472cafe425b91de0c339

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09388195B2