Cyanoacetic acid → N-((5-((2-(2-cyanoacetamido)pyridin-4-yl)oxy)pyridin-2-yl)carbamoyl)pivalamide

Participants

Reaction Steps

A mixture of Example C1 (0.15 g, 0.455 mmol), cyanoacetic acid (0.080 mL, 1.206 mmol), TBTU (0.258 g, 0.804 mmol) and DIEA (0.35 mL, 2.009 mmol) in DMF (5 mL) was stirred at RT overnight, treated with 10% K2CO3, extracted with DCM (4×) and the combined organics were washed with brine, dried over Na2SO4, concentrated to dryness and purified via preparative TLC (MeOH/DCM/TEA) to afford N-((5-((2-(2-cyanoacetamido)pyridin-4-yl)oxy)pyridin-2-yl)carbamoyl)pivalamide (126 mg, 79%). 1H NMR (400 MHz, DMSO-d6): δ 11.24 (s, 1H), 10.92 (s, 1H), 10.44 (s, 1H), 8.26 (d, J=2.9 Hz, 1H), 8.22 (d, J=5.8 Hz, 1H), 8.10 (d, J=9.0 Hz, 1H), 7.75 (dd, J=9.0, 2.9 Hz, 1H), 7.56 (s, 1H), 6.76 (dd, J=5.7, 2.4 Hz, 1H), 3.93 (s, 2H), 1.21 (s, 9H); MS (ESI) m/z: 397.2 (M+H+).

Provenance & Evidence