Réaction #2161271

Équation de réaction

2-methylpropanoyl 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,2-dimethylpropanamide

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 2-methylpropanoyl chloride (32 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, 147 mg, 83%. 1H NMR (mix of rotomers, 400 MHz, DMSO-D6) δ ppm 8.47-8.60 (2 H, m) 7.62-7.72 (2 H, m) 7.31 (2 H, dd, J=8.46, 5.68 Hz) 7.15 (2 H, t, J=8.97 Hz) 6.53 (1 H, s) 5.07-5.35 (2 H, m) 4.43-4.61 (0.5 H, m) 4.38 (1 H, d, J=12.88 Hz) 3.95 (3.5 H, s) 3.05-3.29 (1 H, m) 2.88-3.04 (0.5 H, m) 2.53-2.89 (4.5 H, m) 1.39-1.86 (4 H, m) 0.91-1.08 (6 H, m); m/z (APCI+) for C27H32N5O2F 478.2 (M+H)+.

Source