反应详情

A solution of 7-amino-4-[(3-bromophenyl)amino]quinazoline (J Med Chem, 1995;38:3482) (500 mg, 1.59 mmol), triethylamine (Et3N) (0.60 mL) and dimethylamine pyridine (DMAP) (catalytic) in tetrahydrofuran (THF) (30 mL) was reacted with chloroethanesulfonyl chloride (1.6 mol eq., 2.54 mmol, 265 μL) at 25° C. for 1 hour, stirred under N2. The reaction mixture was diluted with saturated NaHCO3 and extracted with EtOAc. The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, concentrated under reduced pressure, and chromatographed on silica gel eluting with MeOH/CH2Cl2/EtOAc (3:47:50). Crystallization from CH2Cl2/hexane, gave N-[4-[(3-bromophenyl)amino]quinazolin-7-yl]vinylsulfonamide (80 mg, 12%) as a cream powder, mp 218° C. decomposes (dec).

1. extractionextracted with EtOAc
2. washThe combined organic extracts were washed with brine
3. dry with materialdried over anhydrous Na2SO4
4. concentrationconcentrated under reduced pressure
5. customchromatographed on silica gel eluting with MeOH/CH2Cl2/EtOAc (3:47:50)
6. customCrystallization from CH2Cl2/hexane