Hydrochloric Acid → HCID 86712645, compound

Participants

Reaction Steps

HOBt (71 mg, 0.52 mmol), EDCl.HCl (0.11 g, 0.59 mmol) and DIPEA (0.16 mL, 0.90 mmol) were added to a stirred solution of 2-(2-(2-(2-((6-(1-(tert-butoxycarbonyl)piperidin-4-yl)pyridin-3-yl)amino)-5-methylpyrimidin-4-ylethyl)phenyl)acetic acid (A19) (96 mg, 0.18 mmol) in dry DMF (5 mL) under an atmosphere of nitrogen. After 10 minutes ammonium carbonate (174 mg, 1.81 mmol) was added in one portion and the resulting mixture was stirred for 18 hours at room temperature. The volatiles were removed in vacuo and the residue was partitioned between EtOAc (10 mL) and saturated aqueous NaHCO3 (10 mL). The aqueous layer was extracted with EtOAc (2×10 mL) then the combined organic layers were washed with brine (10 mL) and dried over Na2SO4. The volatiles were removed in vacuo and the residue adsorbed onto silica gel and purified by chromatography (Biotage Isolera, 40 g SiO2 cartridge, 0-100% EtOAc in petroleum benzine 40-60° C. followed by 0-25% MeOH in DCM) to give the title compound A20 as a clear oil (72 mg, 75%). 1H NMR (400 MHz, CDCl3) δ 8.82 (d, J=2.4 Hz, 1H), 8.14-8.06 (m, 1H), 7.93 (dd, J=8.5, 2.7 Hz, 1H), 7.37 (s, 1H), 7.26-7.22 (m, 4H), 7.10 (d, J=8.5 Hz, 1H), 5.91 (s, 1H), 5.73 (s, 1H), 4.24 (s, 2H), 3.69 (s, 2H), 3.09 (dd, J=9.7, 6.0 Hz, 2H), 2.97-2.90 (m, 2H), 2.86-2.72 (m, 3H), 2.12 (s, 3H), 1.90 (d, J=12.8 Hz, 2H), 1.68 (m, 2H), 1.47 (s, 9H). LCMS-A: rt 5.018 min; m/z 531 [M+H]+.

Provenance & Evidence