Hydrochloric Acid → HCID 73055447, compound

Participants

Reaction Steps

HOBt (0.032 g, 0.24 mmol), EDCl.HCl (0.045 g, 0.24 mmol) and DIPEA (0.16 mL, 0.91 mmol) were added to a solution of 2-(2-(2-(2-((4-(1-(tert-butoxycarbonyl)piperidin-4-yl)phenyl)amino)-5-methoxypyrimidin-4-yl)ethyl)phenyl)acetic acid (A101) (0.099 g, 0.18 mmol) in dry THF (6 mL) and dry DMF (1 mL) under nitrogen. After 10 minutes ammonium carbonate (0.087 g, 0.91 mmol) was added in one portion and the resulting mixture was stirred at room temperature for 66 hours. The volatiles were removed in vacuo and the residue partitioned between EtOAc (50 mL) and saturated aqueous NaHCO3 (50 mL). The aqueous layer was extracted with EtOAc (2×50 mL). The combined organic layers were washed with brine (50 mL) and dried over MgSO4. The solvent was removed in vacuo and the residue purified by silica gel column chromatography (Biotage Isolera, 24 g SiO2 cartridge, 0-100% EtOAc in petroleum benzine 40-60° C. followed by 0-20% MeOH in EtOAc) to give the title compound A102 as a clear oil (0.094 g, 92%); 1H NMR (400 MHz, d4-MeOH) δ 8.00 (s, 1H), 7.53 (d, J=8.6 Hz, 2H), 7.22 (dd, J=7.0, 3.8 Hz, 1H), 7.20-7.13 (m, 3H), 7.10 (d, J=8.6 Hz, 2H), 4.18 (d, J=13.0 Hz, 2H), 3.78 (s, 3H), 3.65 (s, 2H), 3.10-3.00 (m, 2H), 3.00-2.92 (m, peak obscured, 2H), 2.90-2.71 (m, peak obscured, 2H), 2.62 (tt, J=11.9, 3.2 Hz, 1H), 1.78 (d, J=12.2 Hz, 2H), 1.60-1.49 (m, 2H), 1.47 (s, 9H). LCMS-A: rt 6.20 min; m/z 546.4 [M+H]+.

Provenance & Evidence