Pyridine → HCID 5275155, Verbindung

A solution of 2,4-dihydro-4-(1-naphthalenyl)-3H-1,2,4-triazole-3-thione (129 mg, 0.50 mmol) in DMSO (2 mL) was added slowly to a solution of 2-bromo-N-(2-nitrophenyl)acetamide (113 mg, 0.50 mmol) and pyridine (121 μL, 1.49 mmol) in DMSO (1 mL) at room temperature. The mixture was stirred at room temperature for 18 h, then diluted with water and extracted with EtOAc (50 mL). The organic layer was washed with water (3×) and brine, dried (MgSO4), filtered and concentrated under reduced pressure. A mixture of Et2O and hexane (1:1) was added, the resulting suspension was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by HPLC using a gradient of MeCN/H2O containing TFA (0.06%) (CombiPrep ODS-AQ 50×20 mm, 5μ, 120 Å). The pure fractions were combined and concentrated to give the title compound (4.5 mg, 2% yield).

1. extractionextracted with EtOAc (50 mL)
2. washThe organic layer was washed with water (3×) and brine
3. dry with materialdried (MgSO4)
4. filtrationfiltered
5. concentrationconcentrated under reduced pressure
6. additionA mixture of Et2O and hexane (1:1)
7. additionwas added
8. filtrationthe resulting suspension was filtered
9. concentrationthe filtrate was concentrated under reduced pressure
10. customThe residue was purified by HPLC
11. additioncontaining TFA (0.06%) (CombiPrep ODS-AQ 50×20 mm, 5μ, 120 Å)
12. concentrationconcentrated

ORD-Eintrag

ord-3de7a3f32d4c4aca8d9eab505dd60f75

Quelldatensatz

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07642277B2