Hydrochloric Acid → HCID 86712715, compound

Participants

Reaction Steps

HOBt (0.042 g, 0.31 mmol), EDCl.HCl (0.049 g, 0.31 mmol) and DIPEA (0.204 mL, 1.20 mmol) were added to a solution of 2-(2-(2-(2-((4-(1-(tert-butoxycarbonyl)piperidin-4-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)-5-(trifluoromethyl)phenyl)acetic acid (A108) (0.157 g, 0.240 mmol) in dry DMF (5 mL) and dry THF (5 mL). Ammonium carbonate (113 mg, 1.20 mmol) was then added and the resulting mixture was stirred at room temperature for 3 days. The mixture was diluted with EtOAc and washed with 10% aqueous NaHCO3. The organic layer was dried (MgSO4) and the volatiles removed under reduced pressure. The residue was adsorbed onto silica gel and purified by silica gel column chromatography (SiO2, 0-100% EtOAc in petroleum benzine 40-60° C.) to give the title compound A109 as a colourless solid (0.121 g, 77%); 1H NMR (400 MHz, d4-MeOH) δ 8.56 (s, 1H), 7.60 (m, 3H), 7.55-7.48 (m, 1H), 7.42 (m, 1H), 7.22 (d, J=8.5 Hz, 2H), 4.23 (d, J=13.3 Hz, 2H), 3.76 (s, 2H), 3.26 (m, 2H), 3.14 (m, 2H), 2.95-2.81 (m, 2H), 2.77-2.64 (m, 1H), 1.83 (m, 2H), 1.70-1.54 (m, 2H), 1.50 (s, 9H). LCMS-A: rt 6.671 min; m/z 652.3 [M+H]+.

Provenance & Evidence