3-(Dimethylamino)-1-propanol → 3-(dimethylamino)propyl 4-((2S,4R)-1-acetyl-4-((isopropoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoate

Participants

Reaction Steps

To a solution of 4-((2S,4R)-1-acetyl-4-((isopropoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoic acid (for a preparation see Intermediate 21) (164 mg, 0.400 mmol) and 3-(dimethylamino)propan-1-ol (206 mg, 1.998 mmol) in DMF (3 mL) were added N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (153 mg, 0.799 mmol) and N,N-dimethylpyridin-4-amine (4.88 mg, 0.040 mmol). The resulting mixture was stirred at room temperature for 2 h, the reaction mixture was diluted with water and EtOAc was added. 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 residue was dissolved in a 1:1 MeOH/DMSO mixture and was purified by MDAP (HpH). The appropriate fractions were combined and concentrated under reduced pressure to give 3-(dimethylamino)propyl 4-((2S,4R)-1-acetyl-4-((isopropoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoate (29.3 mg, 15%) as a viscous colourless oil. LCMS (Formate, 2 min), Rt=0.75 min, MH+=476.

Provenance & Evidence