Hydrochloric Acid → HCID 73055749, compound

Participants

Reaction Steps

HOBt (0.074 g, 0.55 mmol), EDCl.HCl (0.117 g, 0.610 mmol) and DIPEA (0.16 mL, 0.94 mmol) were added to a solution of 2-(2-(2-(5-methyl-2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)ethyl)phenyl)acetic acid (A117) (0.066 g, 0.19 mmol) in dry DMF (5 mL) under an atmosphere of nitrogen. After 10 minutes ammonium carbonate (0.180 g, 1.88 mmol) was added in one portion and the resulting mixture stirred for 18 hours at room temperature. The volatiles were removed in vacuo and the residue partitioned between EtOAc (50 mL) and aqueous saturated NaHCO3 (50 mL). The aqueous layer was extracted with EtOAc (2×25 mL). The combined organic layers were washed with brine (25 mL) and dried over Na2SO4. 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 0-30% MeOH in EtOAc) to give the title compound 28 as a yellow solid (0.040 g, 61%); 1H NMR (400 MHz, d6-DMSO) δ 9.18 (s, 1H), 8.10 (s, 1H), 7.86 (s, 1H), 7.43 (s, 2H), 7.28-7.10 (m, 4H), 6.93 (s, 1H), 3.78 (s, 3H), 3.49 (s, 2H), 3.07-2.98 (m, 2H), 2.90-2.81 (m, 2H), 2.04 (s, 3H). LCMS-A: rt 4.464 min; m/z 351 [M+H]+.

Provenance & Evidence