Ethanolamine → HCID 71469143, compound

Participants

Reaction Steps

To a solution of 2-(4-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)phenyl)acetic acid, lithium salt (Intermediate 9)(166 mg, 0.377 mmol) and ethanolamine (0.034 mL, 0.565 mmol) in DMF (3 mL) were added HATU (287 mg, 0.754 mmol) and DIPEA (0.197 mL, 1.131 mmol). The resulting mixture was stirred at room temperature for 1 h, the reaction mixture was diluted with EtOAc and water. The layers were separated and the aqueous phase was extracted with EtOAc (×3). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The crude residue was dissolved in 1:1 MeOH/DMSO and was purified by MDAP (formate). The appropriate fractions were combined and concentrated in vacuo to give 2-(4-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)phenyl)-N-(2-hydroxyethyl)acetamide (21 mg, 11%) as a colourless oil. LCMS (Formate, 2 min), Rt=0.76 min, MH+=484.

Provenance & Evidence