Methyl isonipecotate → HCID 66920876, compound

Participants

Reaction Steps

A mixture of Example 185 (50 mg, 0.15 mmol) and piperidine-4-carboxylic acid methyl ester (0.75 mL) were heated to 140° C. for 20 min. in a microwave reactor. The reaction mixture was extracted with ethyl acetate (5 mL) and washed with 1M HCl (2×10 mL). The organic layer was concentrated in vacuo and purified by silica gel chromatography (50-100% ethyl acetate in hexanes) providing the title compound as an off white solid (34 mg, 52%). 1H NMR (300 MHz, DMSO-d6) δ 8.92 (t, J=6.44 Hz, 1H), 8.05 (d, J=2.03 Hz, 1H), 7.47 (dd, J=8.82, 2.37 Hz, 1H), 7.30 (s, 2H), 7.06 (s, 1H), 6.80 (d, J=8.48 Hz, 1H), 4.48 (q, J=7.12 Hz, 2H), 4.31 (d, J=6.10 Hz, 2H), 4.14 (d, J=13.22 Hz, 2H), 3.60 (s, 3H), 2.82-2.98 (m, 2H), 2.56-2.67 (m, 1H), 1.85 (dd, J=13.56, 3.39 Hz, 2H), 1.43-1.62 (m, 2H), and 1.30 (t, J=7.12 Hz, 3H); MS (ESI) m/e positive ion 461 [M+Na]+, 439 [M+H]+; negative ion 437 [M−H]−.

Provenance & Evidence