Water → 1-{4-[(ethylamino)carbonyl]phenyl}-5-isobutyl-1H-1,2,3-triazole-4-carboxylic acid

Temperature

60 °C

Ethyl 5-methyl-3-oxohexanoate (1.20 g, 6.99 mmol, 1.4 eq.) obtained in Example 93a) and 4-azido-N-ethylbenzamide (1.00 g, 4.99 mmol) were dissolved in ethanol (20 ml), sodium ethoxide (491 mg, 6.49 mmol, 1.3 eq.) was added, and the mixture was stirred at room temperature for 30 min and at 60° C. for 18 hr. Water (20 ml) was added to the reaction mixture, and ethanol was evaporated. The residue was diluted with 2% aqueous sodium carbonate solution (25 ml), and the mixture was washed with ethyl acetate-hexane (2:1, 45 ml). The organic layer was extracted with 1% aqueous sodium carbonate solution (15 ml). The aqueous layers were combined, washed with ethyl acetate-hexane (1:1, 30 ml), acidified (pH<3) with 6N hydrochloric acid and extracted with ethyl acetate (40 ml and 30 ml). The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated, and ethyl acetate was added. The precipitate was collected by filtration, washed with ethyl acetate and diethyl ether and dried to give the title compound as a white powder (1.45 g, 4.58 mmol, 91.7%).

1. customwas evaporated
2. additionThe residue was diluted with 2% aqueous sodium carbonate solution (25 ml)
3. washthe mixture was washed with ethyl acetate-hexane (2:1, 45 ml)
4. extractionThe organic layer was extracted with 1% aqueous sodium carbonate solution (15 ml)
5. washwashed with ethyl acetate-hexane (1:1, 30 ml)
6. extractionextracted with ethyl acetate (40 ml and 30 ml)
7. washwashed with saturated brine
8. dry with materialdried over anhydrous sodium sulfate
9. concentrationconcentrated
10. additionethyl acetate was added
11. filtrationThe precipitate was collected by filtration
12. washwashed with ethyl acetate and diethyl ether
13. customdried

ORD record

ord-b755ccca818b47e2a0cff752cc999a07

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07803822B2