반응 #2161272

반응 방정식

cyclobutanecarbonyl chloride

1-{[5-(4-fluorobenzyl)-3-pyridin-4-yl-1H-pyrazol-1-yl]acetyl}-N-methylpiperidin-4-amine

triethylamine

→

title compound

N-(1-{[5-(4-fluorobenzyl)-3-pyridin-4-yl-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-methylcyclobutanecarboxamide

용매

DCM

반응 조건

후처리

1. 1
   세척eluted with 2-8% MeOH/DCM

실험 절차

To a solution of 1-{[5-(4-fluorobenzyl)-3-pyridin-4-yl-1H-pyrazol-1-yl]acetyl}-N-methylpiperidin-4-amine (150 mg, 0.37 mmol) in DCM (3 mL) at room temperature was added triethylamine (56 μL, 0.40 mmol) followed by cyclobutanecarbonyl chloride (42 μL, 0.37 mmol) and the solution stirred for 10 minutes. The solution was then loaded directly onto a pre-wetted Biotage 25M column for flash chromatography and eluted with 2-8% MeOH/DCM to yield the title compound as a white solid, 154 mg, 85%; 1H NMR (mix of rotomers, 400 MHz, DMSO-D6) δ ppm 8.52 (2 H, d, J=6.06 Hz), 7.66 (2 H, d, J=6.06 Hz), 7.30 (2 H, dd, J=8.46, 5.68 Hz), 7.15 (2 H, t, J=8.97 Hz), 6.52 (1 H, s), 5.08-5.33 (2 H, m), 4.42-4.57 (0.5 H, m), 4.38 (1 H, d, J=13.39 Hz), 3.95 (3 H, s), 3.64-3.79 (0.5 H, m), 3.36-3.48 (0.5 H, m), 3.24-3.34 (0.5 H, m), 3.03-3.20 (1 H, m), 2.55-2.76 (4 H, m), 2.01-2.28 (4 H, m), 1.39-1.99 (6 H, m); m/z (APCI+) for C28H32N5O2F 490.2 (M+H)+.

출처