Hydrochloric Acid → HCID 86712685, compound

Participants

Reaction Conditions

Reaction Steps

HOBt (0.119 g, 0.879 mmol) and EDCl.HCl (0.169 g, 0.879 mmol) were added to a solution of 2-(2-(2-(2-((4-(((tert-butoxycarbonyl)(2-hydroxyethyl)amino)methyl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)acetic acid (A74) (0.421 g, 0.733 mmol) and Et3N (0.408 mL, 0.297 mmol) in DMF (10 mL). After 10 minutes ammonium carbonate (1.34 g, 14.65 mmol) was added and the resulting mixture was stirred at 40° C. for 22 hours. Saturated aqueous saturated NaHCO3 solution (25 mL) was added the resulting mixture extracted with EtOAc (3×15 mL). The combined organic fractions were dried (Na2SO4), filtered and evaporated in vacuo. The residue was adsorbed onto silica gel then purified using column chromatography (CombiFlash Rf, 24 g SiO2 cartridge, 40-100% EtOAc in cyclohexane) to give the title compound A75 as a white solid (0.301 g, 76%); 1H NMR (300 MHz, CDCl3) δ 8.56 (s, 1H), 7.61-7.58 (m, 3H), 7.30-7.26 (m, 6H), 5.48 (brs, 2H), 4.49 (brs, 2H), 3.74 (brs, 4H), 3.42 (brs, 2H), 3.15-3.12 (m, 4H), 1.50 (s, 9H). LCMS-B: rt 7.344 min; m/z 574 [M+H]+.

Provenance & Evidence