Ammonium formate → HCID 70976652, compound

Participants

Reaction Steps

To a flask charged with ethyl 6-((2S,4R)-1-acetyl-2-methyl-4-((5-nitropyridin-2-yl)amino)-1,2,3,4-tetrahydroquinolin-6-yl)nicotinate (for a preparation see Intermediate 25)(780 mg, 1.640 mmol), ammonium formate (1034 mg, 16.40 mmol) and palladium on carbon (10% Pd/C) (160 mg, 1.503 mmol) was added ethanol (15 ml) and the resulting mixture was refluxed for 45 min. The reaction was cooled to room temperature, filtered through Celite™, the residue washed with EtOH and the combined filtrate and washings 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; which gave ethyl 6-((2S,4R)-1-acetyl-4-((5-aminopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)nicotinate (450 mg, 1.010 mmol, 61.6% yield) as a pink foam. LCMS (HpH, 2 min), Rt=0.93 min, MH+=446.

Provenance & Evidence