1-(4-Fluorophenyl)cyclopropan-1-amine hydrochloride → Ammonium Acetate

Participants

Reaction Steps

2-(4-fluorophenyl)-5-(5-(1-(4-fluorophenyl)cyclopropylcarbamoyl)-2-methylphenyl)-N-methylpyrazolo[1,5-a]pyridine-3-carboxamide was prepared from 3-(2-(4-fluorophenyl)-3-(methylcarbamoyl)pyrazolo[1,5-a]pyridin-5-yl)-4-methylbenzoic acid (0.016 g, 0.040 mmol) and 1-(4-fluorophenyl)cyclopropanamine hydrochloride (0.011 g, 0.059 mmol). The resultant residue was purified using preparative HPLC (Waters—Xbridge, 50×100 mm, 5 micron, C18 column; 0.1M ammonium acetate, 10-100% B (B=5% H2O/CH3CN)/A (A=95% H2O/CH3CN), 15 min. gradient) to afford 2-(4-fluorophenyl)-5-(5-(1-(4-fluorophenyl)cyclopropylcarbamoyl)-2-methylphenyl)-N-methylpyrazolo[1,5-a]pyridine-3-carboxamide as a white solid. Preparative HPLC retention time: 10.5 min. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.24 (s, 1H), 8.84 (d, J=7.03 Hz, 1H), 7.83-7.96 (m, 5H), 7.75 (s, 1H), 7.47 (d, J=8.03 Hz, 1H), 7.26-7.38 (m, 4H), 7.05-7.16 (m, 3H), 2.78 (d, J=4.77 Hz, 3H), 2.37 (s, 3H), 1.26 (d, J=6.27 Hz, 4H). LCMS retention time: 2.533 min. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Phenomenex-Luna, 10 micron, C18, 3.0×50 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 4 mL/min, a gradient of 100% solvent A/0% solvent B to 0% solvent A/100% solvent B, a gradient time of 3 min, a hold time of 1 min, and an analysis time of 4 min where solvent A was 10% methanol/90% water/10 mM TFA and solvent B was 10% water/90% methanol/10 mM TFA. MS data was determined using a Micromass Platform for LC in electrospray mode. m/z 537 (MH+).

Provenance & Evidence