Morpholine → Ammonia

An ice-bath cooled solution of 6-bromo-1,2-benzisoxazol-3 (2H)-one (Intermediate 24) (0.15 g) and dry pyridine (0.15 ml) in dry dichloromethane (12 ml) was stirred under nitrogen and treated with triflic anhydride (180 μL). The solution was stirred at room temp. for 90 min, diluted with cyclohexane then applied to a Varian Bond-Elut SPE cartridge (silica, 5 g) and eluted with cyclohexane and dichloromethane to give a colourless oil. The oil was dissolved in acetonitrile (4 ml) treated with morpholine (61 μL) and diisopropylethylamine (0.15 ml) then stirred at 70° under nitrogen for 16 h. The cooled reaction mixture was purified on a Varian Bond-Elut SPE cartridge (silica, 5 g) using dichloromethane:ethanol:0.88 ammonia to give the title compound as a white solid (0.03 g).

1. stirringThe solution was stirred at room temp. for 90 min
2. washeluted with cyclohexane and dichloromethane
3. customto give a colourless oil
4. stirringthen stirred at 70° under nitrogen for 16 h
5. customThe cooled reaction mixture
6. customwas purified on a Varian Bond-Elut SPE cartridge (silica, 5 g)

ORD 기록

ord-3301ce729ef74b4f834a933f9cec8204

출처 데이터셋

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07642276B2