Cumylamine → Ammonium Acetate

Participants

Reaction Steps

To a solution containing 2-phenylpropan-2-amine (0.040 g, 0.29 mmol), diisopropylethylamine (0.10 mL, 0.58 mmol), 3-(2-(4-fluorophenyl)-3-(methylcarbamoyl)pyrazolo[1,5-a]pyridin-5-yl)benzoic acid (0.10 g, 0.20 mmol) and DMF (1.3 mL) was added HATU (0.10 g, 0.25 mmol) in one portion. The solution was maintained at room temperature for 1 h and concentrated. The resultant residue was purified using preparative HPLC (Waters-Xbridge, 50×100 mm, 5 micron, C18 column; 0.1M ammonium acetate, 0-100% B (B=5% H2O/CH3CN)/A (A=95% H2O/CH3CN), 12 min. gradient) afforded 2-(4-fluorophenyl)-N-methyl-5-(3-(2-phenylpropan-2-ylcarbamoyl)phenyl)pyrazolo[1,5-a]pyridine-3-carboxamide as a white solid. Preparative HPLC: retention time: 8.0 mM. 1H NMR (500 MHz, DMSO-D6) δ ppm 8.90 (d, J=7.32 Hz, 1H), 8.65 (s, 1H), 8.26 (s, 1H), 8.10 (s, 1H), 8.00 (d, J=6.10 Hz, 2H), 7.88-7.94 (m, 3H), 7.61-7.66 (m, 1H), 7.49 (dd, J=7.17, 1.68 Hz, 1H), 7.42 (d, J=7.63 Hz, 2H), 7.28-7.35 (m, 4 H), 7.19 (s, 1H), 2.81 (d, J=4.58 Hz, 3H), 1.72 (s, 6H). LCMS: retention time: 3.325 min. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Phenomenex-Luna, 10u, C18, 4.6×50 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 mM, a hold time of 1 min, and an analysis time of 4 min where solvent A was 10% CH3OH/90% H2O/10 mM TFA and solvent B was 10% H2O/90% CH3OH/10 mM TFA. MS data was determined using a Micromass Platform for LC in electrospray mode. m/z 507 (MH+).

Provenance & Evidence