TBAF tetrahydrofuran → HCID 25234232, compound

Participants

Reaction Steps

Preparation of 3-(3-(trifluoromethyl)phenyl)-5-(4-(4-(trifluoromethyl)phenylsulfonyl)-3,4-dihydro-2H-benzo[b][1,4]thiazin-6-yl)-1,2,4-oxadiazole 3-(trifluoromethyl)-N′-(4-(4-(trifluoromethyl)phenylsulfonyl)-3,4-dihydro-2H-benzo[b][1,4]thiazine-6-carbonyloxy)benzimidamide (38.8 mg, 0.066 mmol) was dissolved in THF (0.5 mL) and 1.0M TBAF/THF (0.5 mL, 0.5 mmol). The reaction was allowed to stir at room temperature for 16 hours. The reaction mixture was diluted with EtOAc (1 mL) and water (1 mL). The layers were separated and the aqueous layer was washed with EtOAc (1 mL). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified by flash column chromatography using a gradient elution of hexanes with 10-60% EtOAc to provide 3-(3-(trifluoromethyl)phenyl)-5-(4-(4-(trifluoromethyl)phenylsulfonyl)-3,4-dihydro-2H-benzo[b][1,4]thiazin-6-yl)-1,2,4-oxadiazole (17.6 mg, 0.031 mmol, 45% yield) as a yellow oil. LCMS (+ESI) m/z=572.05 [M+H]+. The compounds listed in Table 6 were prepared using the procedure outlined in the synthesis of the compound of Example 80. These compounds can be prepared from the appropriate intermediate (selected from Intermediates J to L) by treatment with the appropriate amine under the above-described conditions.

Provenance & Evidence