Nicotinic Acid → n-[3-(3-Methyl-4-oxo-5h-2-oxa-1,5,7-triaza-cyclopenta-[a]naphthalen-5-yl)-cyclohexylmethyl]-nicotinamide

Participants

Reaction Steps

Combine 5-(3-aminomethyl-cyclohexyl)-3-methyl-5H-2-oxa-1,5,7-triaza-cyclopenta[a]naphthalen-4-one hydroiodide (136 mg, 0.31 mmol) with nicotinic acid (42 mg, 0.34 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (65 mg, 0.34 mmol), 1-hydroxy-7-azabenzo-triazole (46 mg, 0.34 mmol), and N,N-diisopropylethyl amine (0.20 mL, 1.15 mmol), in N,N-dimethylformamide (4 mL) and stir over a weekend at ambient temperature. Concentrate in vacuo and take up in water and extract with dichloromethane. Dry over sodium sulfate and concentrate in vacuo. Elute over silica gel using methanol/dichloromethane to give 22 mg (17%) of the desired amide as a white solid. MS(EI): Exact Mass Calc'd for: C23H24N5O3 418.1879 m/z. Found: 418.1869 m/z.

Provenance & Evidence