反应详情

To a mixture of 3-(4-aminophenyl)-5-(3-(3-morpholinopropyl)ureido)isothiazole-4-carboxamide (6 mg, 0.015 mmol) and N,N-diisopropylethylamine (0.0078 mL, 0.045 mmol) in 0.8 mL THF at rt was added 3-(trifluoromethyl)benzoyl chloride (0.0024 mL, 0.017 mmol). The reaction was stirred at rt for 2 hours, then quenched with aqueous Na2CO3 solution, stirred 5 min at rt, and then partitioned between EtOAc and aqueous Na2CO3 solution, the EtOAc layer washed with H2O, brine, dried with anhydrous Na2SO4 and rotary evaporated. The solid was chromatographed eluting with CHCl3, then gradient 2.5% to 10% MeOH in CHCl3. The resulting solid was subjected to an EtOAc/NaHCO3 work-up to remove the presence of any silica gel impurity. Upon evaporation of the EtOAc layer the title compound was obtained as a white solid (7 mg, 76%).

1. customquenched with aqueous Na2CO3 solution
2. stirringstirred 5 min at rt
3. custompartitioned between EtOAc and aqueous Na2CO3 solution
4. washthe EtOAc layer washed with H2O, brine
5. dry with materialdried with anhydrous Na2SO4 and rotary evaporated
6. customThe solid was chromatographed
7. washeluting with CHCl3
8. customto remove the presence of any silica gel impurity
9. customUpon evaporation of the EtOAc layer the title compound