(Diethylamino)sulfur trifluoride → 5-(5-Chloro-2-fluoro-phenyl)-3-[4-(2-fluoro-ethyl)-5-thiophen-2-yl-4H-[1,2,4]triazol-3-ylsulfanylmethyl]-[1,2,4]oxadiazole

To a cooled (−15° C.) solution of 2-{3-[5-(5-chloro-2-fluoro-phenyl)-[1,2,4]oxadiazol-3-ylmethylsulfanyl]-5-thiophen-2-yl-[1,2,4]triazol-4-yl}-ethanol (46 mg, 0.11 mmol) in anhydrous THF (15 ml) was dropwise added DAST (32 ml, 0.24 mmol). The mixture was stirred at room temperature for 1.5 h and was then quenched with MeOH (1 ml). The solvent was removed under reduced pressure and the residue was partitioned between brine and EtOAc. The aqueous layer was extracted with EtOAc (2×20 ml). The combined organic layers were washed with brine (10 ml), dried (MgSO4) and concentrated under reduced pressure. Purification by flash chromatography (EtOAc:heptane 2:1) and preparative HPLC afforded the title compound as a white solid (11 mg, 22%). 1H NMR (CDCl3) d (ppm): 8.05 (dd, 1H), 7.52 (m, 3H), 7.20 (m, 1H), 7.16 (m, 1H), 4.75 (t, 1H), 4.63 (m, 3H), 4.45 (m, 2H).

1. customwas then quenched with MeOH (1 ml)
2. customThe solvent was removed under reduced pressure
3. customthe residue was partitioned between brine and EtOAc
4. extractionThe aqueous layer was extracted with EtOAc (2×20 ml)
5. washThe combined organic layers were washed with brine (10 ml)
6. dry with materialdried (MgSO4)
7. concentrationconcentrated under reduced pressure
8. customPurification by flash chromatography (EtOAc:heptane 2:1) and preparative HPLC

ORD-Eintrag

ord-c4fe691e81e24475b26e156b9d2028fe

Quelldatensatz

uspto-grants-2008_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07456200B2