1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-(3-methylbutyl)-1H-1,2,3-triazole-4-carboxamide

1-{4-[(Ethylamino)carbonyl]phenyl}-5-(3-methylbutyl)-1H-1,2,3-triazole-4-carboxylic acid (462 mg, 1.40 mmol) obtained in Example 97b), HOBt (95.4 mg, 0.700 mmol, 0.5 eq.) and cyclopropylamine (0.130 ml, 1.82 mmol, 1.3 eq.) were dissolved in acetonitrile-DMF (2:1, 7.5 ml), WSC (328 mg, 1.68 mmol, 1.2 eq.) was added, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated, and the residue was diluted with ethyl acetate (40 ml) and washed with 2% aqueous sodium carbonate solution (×2), 10% aqueous ammonium chloride solution and saturated brine. The aqueous layers were each extracted with ethyl acetate-hexane (2:1, 30 ml). The organic layers were combined, dried over anhydrous sodium sulfate and concentrated, and diethyl ether was added to the residue. The precipitate was collected by filtration, washed with diethyl ether and dried to give the title compound as a grayish white powder (481 mg, 1.30 mmol, 93.0%).

1. concentrationThe reaction mixture was concentrated
2. additionthe residue was diluted with ethyl acetate (40 ml)
3. washwashed with 2% aqueous sodium carbonate solution (×2), 10% aqueous ammonium chloride solution and saturated brine
4. extractioneach extracted with ethyl acetate-hexane (2:1, 30 ml)
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated
7. additiondiethyl ether was added to the residue
8. filtrationThe precipitate was collected by filtration
9. washwashed with diethyl ether
10. customdried

ORD record

ord-7228865318f8484a9878b3411dc5bf9e

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07803822B2