Morpholine → 1-((2S,4R)-2-methyl-4-(pyridin-2-ylamino)-6-(4-(pyrrolidine-1-carbonyl)phenyl)-3,4-dihydroquinolin-1(2H)-yl)ethanone formate

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Reaction Steps

Crude lithium 4-((2S,4R)-1-acetyl-2-methyl-4-(pyridin-2-ylamino)-1,2,3,4-tetrahydroquinolin-6-yl)benzoate for a preparation see Intermediate 58) (40 mg) and HATU (41 mg, 0.108 mmol) in DMF (0.5 mL) were treated with DIPEA (51.2 μL, 0.294 mmol) and the mixture shaken and sonicated until a solution was formed (<2 min). This solution was added to pyrrolidine (16 μL, 0.192 mmol), the mixture briefly shaken then left to stand at room temperature for 2 h. A further portion of morpholine (32 μL, 0.384 mmol) was added and the mixture left to stand overnight. The mixture was diluted with water and extracted three times with DCM. The combined organic layers were dried by passing through a hydrophobic frit and concentrated in vacuo to give a residue. The residue was purified by MDAP (formate) to give 1-((2S,4R)-2-methyl-4-(pyridin-2-ylamino)-6-(4-(pyrrolidine-1-carbonyl)phenyl)-3,4-dihydroquinolin-1(2H)-yl)ethanone formate (23 mg, 0.046 mmol, 12%) as a pale pink glass. LCMS: (Formate, 2 min), Rt=0.70 min, MH+455

Provenance & Evidence