N,N-Dimethylglycine → 2-Dimethylamino-N-(5-methyl-6-oxo-5,6-dihydro-phenanthridin-8-yl)-acetamide

Participants

Reaction Steps

1-[3-(Dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (EDC) (63 mg, 0.33 mmol) was added in one portion to a solution of 8-amino-5-ethyl-5H-phenanthridin-6-one I-16c (65 mg, 0.27 mmol), N,N-dimethylglycine (34 mg, 0.33 mmol) 4-dimethylaminopyridine (7 mg, 0.054 mmol), and triethylamine (0.076 ml, 0.55 mmol) in dichloromethane (5 ml). The resultant solution was stirred at 23° C. for 16 hours and diluted with 1:1 ethyl acetate/hexanes (20 ml). The reaction mixture was washed with water (25 ml) and saturated aqueous ammonium chloride (25 ml) and dried over anhydrous magnesium sulfate and concentrated. The residue was purified by rotary chromatography on silica gel (dichloromethane grading to 5% methanol/dichloromethane) to provide 2-dimethylamino-N-(5-methyl-6-oxo-5,6-di hydro-phenanthridin-8-yl)-acetamide 16A (28 mg, 33%) as a yellow oil.

Provenance & Evidence