Hydrochloric Acid → HCID 86712641, compound

Participants

Reaction Steps

HOBt (76 mg, 0.56 mmol) and EDCl.HCl (108 mg, 0.561 mmol) were added to a solution of 2-(2-(2-(2-((4-(((tert-butoxycarbonyl)amino)methyl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)acetic acid (A15) (251 mg, 0.468 mmol) and DIPEA (326 μL, 1.87 mmol) in DMF (2 mL) and THF (10 mL). The resulting mixture was stirred at room temperature overnight then the volatiles were removed in vacuo and the residue partitioned between EtOAc (150 mL) and saturated aqueous NaHCO3 (100 mL). The layers were separated and the organic layer was washed with water (100 mL), brine (50 mL) and dried over MgSO4. The volatiles were removed in vacuo and the residue adsorbed onto silica gel and purified by silica gel column chromatography (Biotage Isolera, SiO2 cartridge, 0-100% EtOAc in petroleum benzine 40-60° C.) to give the title compound A16 as a tan solid (0.22 g, 89%); 1H NMR (400 MHz, d6-DMSO) δ 10.18 (s, 1H), 8.67 (s, 1H), 7.68 (d, J=8.5 Hz, 2H), 7.43 (s, 1H), 7.33 (t, J=6.0 Hz, 1H), 7.27-7.10 (m, 6H), 6.91 (s, 1H), 3.50 (s, 2H), 3.18 (d, J=5.3 Hz, 2H), 3.14-2.99 (m, 4H), 1.40 (s, 9H). LCMS-A: rt 6.086 min; m/z 530 [M+H]+.

Provenance & Evidence