Ethanolamine → HCID 71469144, compound

Participants

Reaction Steps

To a solution of 3-(4-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)phenyl)propanoic acid (for a preparation see Intermediate 10)(44 mg, 0.097 mmol) and ethanolamine (0.012 mL, 0.194 mmol) in DMF (3 mL) were added HATU (55.2 mg, 0.145 mmol) and DIPEA (0.051 mL, 0.290 mmol). The resulting mixture was stirred for 40 min, then partitioned between water and EtOAc. 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 3-(4-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)phenyl)-N-(2-hydroxyethyl)propanamide (22.8 mg, 47%) as a, viscous yellow oil. LCMS (Formate, 2 min), Rt=0.80 min, MH+=498.

Provenance & Evidence