4-Hy­droxy-5-meth­oxy-N,1-dimethyl-2-oxo-N-[4-(tri­fluoro­meth­yl)phen­yl]-1,2-di­hydro­quinoline-3-carboxamide

The title compound, C₂₀H₁₇F₃N₂O₄, named tasquinimod, is a second-generation oral quinoline-3-carboxamide analogue, which is currently in phase III clinical trials for the treatment of metastatic prostate cancer. The quinoline unit is almost planar (r.m.s. deviation of fitted atoms = 0.0075 Å). The carboxamide side chain, substituted at position 3, is tilted by 88.07 (7)° to the quinoline plane. Both the methyl and carbonyl groups of this carboxamide side chain are in a syn conformation. The 4-(tri­fluoro­meth­yl)phenyl plane is inclined at 50.62 (17)° to the plane of the carboxamide side chain, and at 87.14 (4)° to the plane of the quinoline ring system. The 4-hy­droxy H atom acts as a double proton donor in an intra­molecular hydrogen bond to the 5-position meth­oxy O atom and in an inter­molecular contact to the 2-oxo group, generating a chain along [010] in the crystal structure.