Hydrochloric Acid → HCID 86712630, compound

Participants

Reaction Steps

HOBt (24 mg, 0.17 mmol), EDCl.HCl (33 mg, 0.17 mmol) and DI PEA (0.12 mL, 0.67 mmol) were added to a stirred solution of 2-(2-(2-(2-((4-(4-((benzyloxy)carbonyl)piperazin-1-yl)phenyl)amino)pyrimidin-4-yl)ethyl)phenyl)acetic acid (A5) (74 mg, 0.13 mmol) in dry THF (5 mL) and dry DMF (2 mL) under an atmosphere of nitrogen. After 10 minutes ammonium carbonate (65 mg, 0.67 mmol) was added and stirring was continued at room temperature for 18 hours. The volatiles were removed in vacuo and the residue was diluted with EtOAc (65 mL) and saturated NaHCO3 (65 mL). The aqueous layer was extracted with EtOAc (2×50 mL) then the combined organic layers were washed with brine (50 mL) and dried over Na2SO4. After filtration the solvent was removed in vacuo to afford a pale yellow solid which was purified by silica gel column chromatography (Biotage Isolera, SiO2 cartridge, 0-100% EtOAc in petroleum benzine 40-60° C.) to give the title compound A6 as brown oil (70 mg, 95%); 1H-NMR (400 MHz, CDCl3) δ 8.20 (s, 1H), 7.64 (s, 1H), 7.48 (d, J=8.9 Hz, 2H), 7.37 (d, J=4.3 Hz, 4H), 7.32 (m, 1H), 7.25-7.17 (m, 4H), 6.91 (d, J=9.0 Hz, 2H), 6.51 (d, J=4.9 Hz, 1H), 5.77 (s, 1H), 5.51 (s, 1H), 5.16 (s, 2H), 3.69-3.64 (m, 4H), 3.64 (s, 2H), 3.11-3.06 (m, 4H), 3.05 (dd, J=9.6, 6.5 Hz, 2H), 2.91-2.84 (m, peak obscured), 2.07 (t, J=7.0 Hz 1H). LCMS-A: rt 5.646 min; m/z 551.2 [M+H]+.

Provenance & Evidence