反应详情

温度

80 °C

A sealable vial was charged with 3-(3-chlorophenyl)-N-(2,4-dimethoxybenzyl)-2-oxo-N-(1,3,4-thiadiazol-2-yl)-2,3-dihydrobenzo[d]oxazole-6-sulfonamide (38 mg, 0.068 mmol), and an aqueous solution of sodium hydroxide (2549 μL, 5.10 mmol) was added. The mixture was heated at 80° C. for 1 h, then poured into sat. aq. NH4Cl. The solution became heterogeneous, extracted with DCM, product did not go into organic layer, even after addition of brine. Aqueous layer was lyophilized to give product along with salts. The mixture was dissolved in MeOH and filtered to remove the majority of salts. The filtrate was concentrated onto Celite® (diatomaceous earth) and eluted through a pre-equilibrated C18 silica gel column (12 g) and eluted with a gradient of 95:5 1% formic acid in water: 1% formic acid in MeCN—10:90 1% formic acid in water: 1% formic acid in MeCN, followed by 100% IPA wash. The fractions containing desired product were concentrated to provide 4-((3-chlorophenyl)amino)-3-hydroxy-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamide formate as a white amorphous solid. m/z (ESI) 383.1 (M+H)+.

1. extractionextracted with DCM, product
2. additioneven after addition of brine
3. customto give product along with salts
4. filtrationfiltered
5. customto remove the majority of salts
6. concentrationThe filtrate was concentrated onto Celite® (diatomaceous earth)
7. washeluted through a pre-equilibrated C18 silica gel column (12 g)
8. washeluted with a gradient of 95:5 1% formic acid in water
9. washwash
10. additionThe fractions containing desired product
11. concentrationwere concentrated