Triethylamine → N-(4-fluorophenyl)-N'-(4-{[1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]oxy}phenyl)cyclopropane-1,1-dicarboxamide

Participants

Reaction Steps

To a round bottom flask equipped with a magnetic stir bar was added 4-[1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy]-phenylamine (0.199 g, 0.63 mmol, 1.0 eq.), 1-(4-fluoro-phenylcarbamoyl)-cyclopropanecarboxylic acid (0.213 g, 0.95 mmol, 1.5 eq), HATU (0.607 g, 1.6 mmol, 2.5 eq), triethylamine (0.26 ml, 1.9 mmol, 3 eq), and anhydrous DMF (5 ml). The mixture was stirred at room temperature for 1 hour. The mixture was diluted with ethyl acetate, washed with (2×) H2O (50 ml), sat'd NaHCO3 (2×), 5% LiCl (3×), sat'd NaCl (1×), dried (Na2SO4), and concentrated in vacuo to give N-(4-fluorophenyl)-N′-(4-{[1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]oxy}phenyl)cyclopropane-1,1-dicarboxamide as a white solid (0.312 g, 95% yield). 1H NMR (400 MHz, CDCl3): 9.21 (s, 1H), 8.82 (bs, 1H), 8.56 (s, 1H), 7.96 (s, 2H), 7.65 (dd, 2H), 7.48 (m, 2H), 7.21 (m, 2H), 7.05 (t, 2H), 6.05 (dd, 1H), 3.78 (m, 1H), 2.61 (m, 1H), 2.16 (m, 1H), 2.14 (s,1H), 1.99 (m, 1H), 1.81 (m, 2H), 1.69 (m, 4H), 1.60 (s, 1H); MS (ESI) for C27H25FN7O4: 517 (MH+).

Provenance & Evidence