Benzoic Acid → n-[3-(3-Methyl-4-oxo-5h-2-oxa-1,5,6-triaza-cyclopenta[a]naphthalen-5-yl)-cyclohexylmethyl]-benzamide

Participants

Reaction Steps

Combine 5-(3-aminomethyl-cyclohexyl)-3-methyl-5H-2-oxa-1,5,6-triaza-cyclopenta[a]naphthalen-4-one hydroiodide (100 mg, 0.23 mmol) with benzoic acid (28 mg, 0.23 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (44 mg, 0.23 mmol), 1-hydroxy-7-azabenzo-triazole (31 mg, 0.23 mmol), and N,N-diisopropylethyl amine (0.12 mL, 0.69 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 ethyl acetate. Dry over sodium sulfate and concentrate in vacuo. Eluted over silica gel using methanol/dichloromethane to give 72 mg (75%) of the desired amide as an off white solid. MS(ES): (M+1)+ 417.2, 418.2 m/z.

Provenance & Evidence