Nicotinic Acid → n-[3-(3-Methyl-oxo-5h-2-oxa-1,5,8-triaza-cyclopenta-[a]naphthalen-5-yl)-cyclohexylmethyl]-nicotinamide

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Reaction Steps

Combine 5-(3-aminomethyl-cyclohexyl)-3-methyl-5H-2-oxa-1,5,8-triaza-cyclopenta[a]naphthalen-4-one hydroiodide (145 mg, 0.31 mmol) with nicotinic acid (45 mg, 0.36 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (70 mg, 0.36 mmol), 1-hydroxy-7-azabenzo-triazole (49 mg, 0.36 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. Eluted over silica gel using methanol/dichloromethane to give 115 mg (83%) of the desired amide as a solid. MS(ES): (M+1)+ 418.0,419.0 m/z.

Provenance & Evidence