Cyclohexylamine → HCID 86704195, compound

Participants

Reaction Conditions

Reaction Steps

N-{3-[2-bromo-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, 0.09 mmol) was dissolved in 3 mL of dimethylacetamide and 74 μL (0.85 mmol) of cyclohexylamine were added. The mixture was stirred at 110° C. for 16 h. The solvent was evaporated under reduced pressure and the residue was taken up with DCM and washed with brine. The organic layer was dried over Na2SO4 and evaporated, giving N-{3-[2-(cyclohexylamino)-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 treated with 4 mL of TFA and 1 mL of water and stirred at 75° C. for 8 h. The solvent was then removed, the residue taken up with DCM and washed with aqueous NaHCO3. The organic layer was dried over Na2SO4 and evaporated. The crude was purified by flash chromatography eluted with cyclohexane-ethanol 9/1, affording 20 mg (42%) of the title compound.

Provenance & Evidence