Synthesis of Deprotected Amine Derivative
Example 3
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Combined tert-butyl 2-[1-[2-[3-(1-cyano-1-methyl-ethyl)phenyl]-6-methyl-4-oxo-chromen-8-yl]ethylamino]benzoate (110.0 mg, 210.5 μmol) and TFA (3.0 g, 2.0 mL, 26 mmol) in DCM (2 mL) and heated at 40° C. for 3 hours. Concentrated the reaction and purified using a C-18 column, eluted with 10-90% acetonitrile in water (0.1% TFA additive), to give the product (45.0 mg, 46%). MS ES+ m/z 467 [M+H]+.
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US11873295B2. Allosteric chromenone inhibitors of phosphoinositide 3-kinase (PI3K) for the treatment of disease (2024-01-16). Petra Pharma Corporation [US]. Inventors: Erin Danielle Anderson [US], Sean Douglas Aronow [US], Nicholas A. Boyles [US], Surendra Dawadi [US], Eugene R. Hickey [US], Thomas Combs Irvin [US], Edward A. Kesicki [US], Gabrielle R. Kolakowski [US], Jennifer Lynn Knight [US], Manoj Kumar [US], Katelyn Frances Long [US], Christopher Glenn Mayne [US], Alfredo Picado [US], Gerit Maria Pototschnig [US], Michael Brian Welch [US], Tien Widjaja [US], Xiaohong Chen [US], Nathan Edward Wright [US], Hua-Yu Wang [US].