Hydrochloric Acid → HCID 86712671, compound

Participants

Reaction Steps

HOBt (49 mg, 0.36 mmol), EDCl.HCl (69 mg, 0.36 mmol) and DIPEA (0.21 mL, 1.2 mmol) were added to a stirred solution of 2-(2-(2-(2-((4-(1-(tert-butoxycarbonyl)piperidin-4-yl)phenyl)amino)-5-methylpyrimidin-4-yl)ethyl)phenyl)acetic acid (A55) (127 mg, 0.239 mmol) in dry THF (6 mL) and dry DMF (1 mL) under an atmosphere of nitrogen. After 10 minutes ammonium carbonate (115 mg, 1.20 mmol) was added in one portion and the resulting mixture was stirred at room temperature for 24 hours. The volatiles were removed in vacuo then the residue was partitioned between EtOAc (50 mL) and saturated aqueous NaHCO3 (50 mL). The layers were separated and the aqueous phase was extracted with EtOAc (2×50 mL). The organic extracts were combined, washed with brine and dried over MgSO4. The volatiles were removed under reduced pressure and the residue purified by column chromatography (0-100% EtOAc in petroleum benzine 40-60° C.) to give the title compound A56 as an off-white solid (66 mg, 52%); 1H NMR (400 MHz, d6-DMSO) δ 9.36 (s, 1H), 8.25-8.16 (m, 1H), 7.74 (d, J=8.7 Hz, 2H), 7.49 (s, 1H), 7.28 (m, 1H), 7.25-7.14 (m, 5H), 7.00 (s, 1H), 4.14 (m, 2H), 3.56 (s, 2H), 3.17-3.04 (m, 2H), 2.98-2.91 (m, 2H), 2.84 (m, 2H), 2.71-2.60 (m, 1H), 2.13 (s, 3H), 1.79 (d, J=11.7 Hz, 2H), 1.59-1.43 (m, 11H). LCMS-A: rt 6.078 min; m/z 530 [M+H]+.

Provenance & Evidence