Triethylamine → HCID 178513618, compound

Temperature

-10 °C

A solution of 0.81 g (7.5 mmol) of ethyl chloroformate in 5 ml of tetrahydrofuran was added dropwise to a solution of 0.85 g (7.5 mmol) of isoxazole-5-carboxylic acid and 3.79 g (37.5 mmol) of triethylamine in 50 ml of tetrahydrofuran at −10° C. After stirring at −10° C. for 1 hour, 1.68 g (7.5 mmol) of 2,3-diaminobenzamide were added. The reaction mixture was stirred at room temp. for 16 hours. The reaction mixture was then concentrated in vacuo. The residue was partitioned between methylene chloride and saturated sodium bicarbonate solution. The aqueous phase was extracted with methylene chloride. The combined organic phases were dried over magnesium sulfate. The residue obtained after concentration in vacuo was taken up in 10 ml of glacial acetic acid and stirred at 100° C. for 60 minutes. The reaction mixture was concentrated in vacuo, and the residue was partitioned between ethyl acetate and saturated sodium bicarbonate solution. The organic phase was dried over magnesium sulfate and concentrated in vacuo. The residue was taken up in isopropanol, and the precipitate produced with petroleum ether was filtered off, washed with petroleum ether and dried in vacuo at 35° C. 120 mg of yellow crystals were obtained.

1. stirringThe reaction mixture was stirred at room temp. for 16 hours
2. concentrationThe reaction mixture was then concentrated in vacuo
3. customThe residue was partitioned between methylene chloride and saturated sodium bicarbonate solution
4. extractionThe aqueous phase was extracted with methylene chloride
5. dry with materialThe combined organic phases were dried over magnesium sulfate
6. customThe residue obtained
7. concentrationafter concentration in vacuo
8. stirringstirred at 100° C. for 60 minutes
9. concentrationThe reaction mixture was concentrated in vacuo
10. customthe residue was partitioned between ethyl acetate and saturated sodium bicarbonate solution
11. dry with materialThe organic phase was dried over magnesium sulfate
12. concentrationconcentrated in vacuo
13. customthe precipitate produced with petroleum ether
14. filtrationwas filtered off
15. washwashed with petroleum ether
16. customdried in vacuo at 35° C

ORD record

ord-4580dd66bb564dcd98e837182441d9bc

Source dataset

uspto-grants-2004_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06696437B1