Ethyl isocyanate → HCID 86704197, compound

Participants

Reaction Conditions

Reaction Steps

N-{3-[2-amino-5-(pyridin-4-yl)-1,3-thiazol-4-yl]-2,4-difluorophenyl}-2,5-difluoro-N-(methoxymethyl)benzenesulfonamide (prepared as described in Example 3, 50 mg, 0.1 mmol) was dissolved in 2 mL of dry 1,4-dioxane and a total amount of 320 μL (4 mmol) of ethylisocyanate were added portionwise until the reaction was complete. The solution was heated at 80° C. under stirring for 18 h. The solvent was then removed and the residue taken up with DCM and washed with water. The organic phase was dried over Na2SO4 and evaporated to dryness, giving N-(3-{2-[(ethylcarbamoyl)amino]-5-(pyridin-4-yl)-1,3-thiazol-4-yl}-2,4-difluorophenyl)-2,5-difluoro-N-(methoxymethyl)benzenesulfonamide. The latter, without any further purification, was dissolved in 9 mL of TFA and 1 mL of water and the resulting mixture was maintained at 60° C. under stirring for 8 h. The solvent was evaporated and the residue taken up with DCM and washed with aqueous NaHCO3. The organic layer was then dried over Na2SO4 and evaporated again. The product was purified by flash chromatography on a silica gel precoated column eluted with DCM-MeOH 95/5, affording, after trituration with diethylether-diisopropyl ether, 17 mg (31%) of the title compound.

Provenance & Evidence