Réaction #2161275

Équation de réaction

methyl chloroformate

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

triethylamine

→

title compound

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

Solvants

DCM

Conditions de réaction

Traitement

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

Mode opératoire

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 methyl chloroformate (29 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, 122 mg, 71%. 1H NMR (400 MHz, DMSO-D6) δ ppm 8.52 (2 H, d, J=4.80 Hz), 7.66 (2 H, d, J=5.05 Hz), 7.30 (2 H, dd, J=8.34, 5.81 Hz), 7.15 (2 H, t, J=8.72 Hz), 6.52 (1 H, s), 5.10-5.27 (2 H, m), 4.38 (1 H, d, J=12.63 Hz), 3.99-4.16 (1 H, m), 3.85-4.00 (3 H, m), 3.59 (3 H, s), 3.04-3.16 (1 H, m), 2.70 (3 H, s), 2.56-2.67 (1 H, m), 1.41-1.75 (4 H, m); m/z (APCI+) for C25H28N5O3F 466.2 (M+H)+.

Source