Reacción #1591773

Ecuación de reacción

1-(5-carbamoylpyridin-2-yl)-piperidin-4-yl 4-nitrophenyl carbonate

1-isopropylpiperazine

DIPEA

→

title compound

Rendimiento 50.0%

1-(5-carbamoylpyridin-2-yl)piperidin-4-yl 4-isopropylpiperazine-1-carboxylate

Rendimiento 50.0%

Disolventes

pyridine

Condiciones de reacción

Tratamiento posterior

1. 1
   Concentraciónwas concentrated to dryness
2. 2
   OtroThe residue was further purified by silica gel chromatography (DCM: MeOH=50:1 to 5:1)

Procedimiento

To the solution of 1-(5-carbamoylpyridin-2-yl)-piperidin-4-yl 4-nitrophenyl carbonate (3.0 g, 7.77 mmol) in pyridine (50 ml) was added 1-isopropylpiperazine (1.05 g, 8.16 mmol) and DIPEA (2.01 g, 15.5 mmol). The resulting mixture was stirred at 30° C. for 2 h before it was concentrated to dryness. The residue was further purified by silica gel chromatography (DCM: MeOH=50:1 to 5:1) to afford the title compound as a white solid (1.46 g, 50%). MP: 200.1-203.6° C. [1H NMR (DMSO, 500 MHz): δ 8.61 (d, J=2 Hz, 1H), 7.95 (dd, J=2.5 Hz, 9 Hz, 1H), 7.53 (s, 1H), 7.12 (s, 1H), 6.87 (d, J=9.5 Hz, 1H), 4.83 (m, 1H), 3.90-3.85 (m, 2H), 3.54-3.49 (m, 2H), 3.34 (s, 4H), 2.67-2.64 (m, 1H), 2.38 (m, 4H), 1.89-1.85 (m, 2H), 1.58-1.54 (m, 2H), 0.95 (d, J=6.5 Hz, 6H); LCMS RtA=1.61 min, [M+H]+=376.3].

Fuente