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Synthesis of thiohydantoin core of apalutamide and late-stage amide formation. Reaction conditions: (a) cyclobutanone, NaCN, AcOH; (b) 17, 1,1′-thiocarbonylbis(pyridine-2(1H)-one, toluene, 100 °C then HCl, EtOH, DMA, 70 °C; (c) n-C5H11MgBr, THF, CO2, then CDI, MeNH2, THF; or Pd(t-Bu3P)2, CO (5 bar), i-Pr2Net, MeNH2, THF, 60 °C; or Pd(OAc)2, dppf, i-Pr2NH, CO, MeOH, 60 °C, then MeNH2, MeOH.
