Reaction #2161277

Reaction equation

cyclobutanecarbonyl chloride

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

triethylamine

→

title compound

N-(1-{2-[5-(4-fluorobenzyl)-3-pyridin-4-yl-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)cyclobutanecarboxamide

Solvents

DCM

Conditions

Workup

1. 1
   Washeluted with 2-8% MeOH/DCM

Procedure

To a solution of 1-{[5-(4-fluorobenzyl)-3-pyridin-4-yl-1H-pyrazol-1-yl]acetyl}piperidin-4-amine (150 mg, 0.38 mmol) in DCM (4 mL) at room temperature was added triethylamine (56 μL, 0.40 mmol) followed by cyclobutanecarbonyl chloride (43 μL, 0.38 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, 138 mg, 76%. 1H NMR (400 MHz, DMSO-D6) δ ppm 8.43-8.56 (2 H, m), 7.60-7.70 (3 H, m), 7.24-7.35 (2 H, m), 7.09-7.21 (2 H, m), 6.51 (1 H, s), 5.09-5.31 (2 H, m), 4.13 (1 H, d, J=13.39 Hz), 3.93 (2 H, s), 3.70-3.88 (2 H, m), 3.15 (1 H, t, J=11.37 Hz), 2.89-3.04 (1 H, m), 2.69-2.82 (1 H, m), 2.03-2.17 (2 H, m), 1.93-2.03 (2 H, m), 1.81-1.92 (1 H, m), 1.66-1.80 (3 H, m,) 1.29-1.48 (1 H, m), 1.13-1.27 (1 H, m); m/z (APCI+) for C27H30N5O2F 476.2 (M+H)+.

Source