Ammonium formate → HCID 70976489, compound

Participants

Reaction Steps

To a flask charged with methyl 4-((2S,4R)-1-acetyl-2-methyl-4-((5-nitropyridin-2-yl)amino)-1,2,3,4-tetrahydroquinolin-6-yl)benzoate (for a preparation see Intermediate 20)(2.43 g, 5.28 mmol), ammonium formate (3.33 g, 52.8 mmol) and palladium on carbon (0.562 g, 5.28 mmol) was added MeOH (50 mL) and the resulting mixture was refluxed for 30 min. The reaction was cooled to room temperature, filtered through Celite™ and the residue washed with MeOH then DMF. The methanolic filtrate and washings were combined and concentrated in vacuo. The residue was dissolved in EtOAc, washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by chromatography eluting with a MeOH/DCM gradient to give methyl 4-((2S,4R)-1-acetyl-4-((5-aminopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoate (2.0 g, 4.65 mmol, 88% yield) as a dark pink foam. LCMS (HpH, 2 min), Rt=0.94 min, MH+=431.

Provenance & Evidence