Reaktion #2161275

Reaktionsgleichung

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

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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)+.

Quelle