Serinol → HCID 71469145, 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 (for a preparation see Intermediate 9)(169 mg, 0.384 mmol) and 2-aminopropane-1,3-diol (69.9 mg, 0.767 mmol) in DMF (2 ml) were added HATU (190 mg, 0.499 mmol) and DIPEA (0.201 mL, 1.151 mmol). The resulting mixture was stirred at room temperature for 2 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-(1,3-dihydroxypropan-2-yl)acetamide (83 mg, 42%) as a colourless oil. LCMS (Formate, 2 min), Rt=0.73 min, MH+=514.

Provenance & Evidence