3-Aminopyridine → 4-Methyl-1-oxo-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole-7-carboxylic acid pyridin-3-ylamide

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Reaction Steps

To a solution of 4-methyl-1-oxo-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole-7-carboxylic acid (step f) (20 mg, 0.08 mmol) in 1 mL of DMF was added HATU (34.3 mg, 0.082 mmol), HOAt (6, 0.04 mmol) and diisopropylethylamine (29 uL, 0.164 mmol). After 15 min, 3-amino-pyridine in 1 mL of DMF was added. The mixture was stirred at room temperature for 48 h. The reaction was extracted with EtOAc several times, washed with water and brine. The combined organics were dried over MgSO4, filtered, and concentrated in vacuum. Purification by silica gel chromatography gave 23 mg of 4-methyl-1-oxo-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole-7-carboxylic acid pyridin-3-ylamide 87% as a white solid. ESI-MS m/z 321.34 [M+H]+.

Provenance & Evidence