Diisopropylethylamine → HCID 86638751, compound

Participants

Reaction Steps

TBTU (2.86 g, 8.9 mmol) and diisopropylethylamine (1.55 mL, 8.9 mmol) were added to a mixture of 1-{[(1,1-dimethylethyl)oxy]carbonyl}-4-piperidinecarboxylic acid (1.35 g, 5.9 mmol) in DMF (20 mL) at ambient temperature. The mixture was stirred at ambient temperature for 1 h, charged with 6-bromo-3-pyridinamine (1.13 g, 6.5 mmol), then stirred at 50° C. overnight. The mixture was cooled to ambient temperature, charged with water (200 mL), and extracted with EtOAc. The organics were dried over MgSO4, filtered, and the filtrate was concentrated. The crude product was purified by chromatography on a silica gel column using 0 to 50% EtOAc/hexanes to give 1.75 g (77%) of 1,1-dimethylethyl 4-{[(6-bromo-3-pyridinyl)amino]carbonyl}-1-piperidinecarboxylate as an off-white solid. 1H NMR (400 MHz, CDCl3): δ 8.32 (d, 1H, J=2.7 Hz), 8.07 (dd, 1H, Ja=8.6 Hz, Jb=2.8 Hz), 7.44-7.39 (m, 2H), 4.16 (bs, 2H), 2.90-2.65 (m, 2H), 2.45-2.35 (m, 1H), 1.95-1.80 (m, 2H), 1.79-1.65 (m, 2H), 1.44 (s, 9H); LRMS (ESI), m/z 384 (M+H).

Provenance & Evidence