1,2-Dichloroethane → HCID 25142331, compound

Participants

Reaction Conditions

Reaction Steps

To a cold (ice bath) mixture of 2-(1-tert-butyl-piperidin-4-yl)-N-phenyl-acetamide (250 mg, 0.91 mmol) and 2,6-dimethylpyridine (0.139 ml, 1.2 mmol) in 1,2-dichloroethane (8 ml) oxalyl chloride (0.07 ml, 0.8 mmol) was added and stirred at 0° C. for 15 min. 2-Chloro-6-({[(S)-cyclopropyl-(3-fluoro-phenyl)-methyl]-carbamoyl}-methyl)-benzoic acid (70 mg, 0.2 mmol) was added and the reaction mixture was stirred in a sealed vessel at 90° C. for 15 hours. It was partitioned between 0.5 M aq. NaOH (40 ml) and ethyl acetate (200 ml), the organic phase washed with water, dried and evaporated. The residue was purified by flash chromatography (SiO2, ethyl acetate-methanol) to give 19 mg of the title compound. LC-MS (m/z) 600.6 (MH+); tR=1.1. 1H NMR (500 MHz, r.t., DMSO-d6): broad signals, a mixture of two atropisomers.

Provenance & Evidence