Methyl chloroformate → HCID 86617957, compound

Participants

Reaction Steps

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)+.

Provenance & Evidence