Acetyl chloride → HCID 59275467, compound

Participants

Reaction Steps

4-amino-2-(4-fluorophenyl)-N-methyl-5-(3-(2-phenylpropan-2-ylcarbamoyl)phenyl)benzofuran-3-carboxamide (20 mg, 0.038 mmol) was diluted in pyridine (1 mL) and treated with excess acetyl chloride (10 μL). The reaction was allowed to stir for 2 hours. The mixture was concentrated and diluted with MeOH (1 mL). The product began to crash out, it was sonicated and filtered and washed with MeOH to afford the titled compound (8 mg, 34%). 1H NMR (500 MHz, DMSO-d6) δ ppm 9.41 (1 H, s), 8.43 (1 H, s), 8.31-8.38 (1 H, m), 7.88-7.92 (1 H, m), 7.82-7.87 (2 H, m), 7.80 (1 H, d, J=7.63 Hz), 7.71 (1 H, d, J=8.55 Hz), 7.54-7.60 (1 H, m), 7.43-7.49 (2 H, m), 7.36-7.43 (5 H, m), 7.28 (2 H, t, J=7.78 Hz), 7.17 (1 H, t, J=7.32 Hz), 2.76 (3 H, d), 1.79 (3 H, s), 1.69 (6 H, s). LC-MS retention time 1.42 min; m/z 564 (MH+). LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Waters XBridge 5 u 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 5 ml/min, a gradient of 100% solvent A/0% solvent B to 0% solvent A/100% solvent B, a gradient time of 2 min, a hold time of 1 min, and an analysis time of 3 min where solvent A was 5% acetonitrile/95% H2O/10 mM ammonium acetate and solvent B was 5% H2O/95% acetonitrile/10 mM ammonium acetate. MS data was determined using a Micromass Platform for LC in electrospray mode. Additional HPLC method: Solvent A=5% CH3CN/95% H2O/0.1% TFA, Solvent B=95% CH3CN/5% H2O/0.1% TFA, Start % B=10, Final % B=100, Gradient time=15 min, Stop time=18 min, Flow Rate=1 ml/min. Column: Waters Sunfire C-18, 4.6×150 mm, 3.5 μm, Rt=12.00 min, purity=96%; Column: Waters Xbridge Phenyl column 4 6×150 mm, 3.5 μm, Rt=11.26 min, purity=95%.

Provenance & Evidence