Benzoic Acid → HCID 22170170, compound

Participants

Reaction Steps

Dissolve [3-(9-chloro-3-methyl-4-oxo-5H-2-oxa-1,5,7-triaza-cyclopenta[a]naphthalen-5-yl)-cyclohexylmethyl]-carbamic acid benzyl ester (310 mg, 0.64 mmol) in dry dichloromethane (8 mL). Add iodotrimethylsilane (0.23 mL, 1.62 mmol) and stir overnight at ambient temperature. Quench with methanol (5 mL) and concentrate in vacuo. Concentrate twice from diethyl ether and use the dark solid crude amine salt directly without purification. MS(ES): (M+1)+ 347.1 m/z. Combine this amine salt with benzoic acid (94 mg, 0.77 mmol),1-[3-(dimethylamino)-propyl]-3-ethylcarbodiimide hydrochloride (148 mg, 0.77 mmol), 1-hydroxy-7-azabenzo-triazole (105 mg, 0.77 mmol), and N,N-diisopropylethyl amine (0.45 mL, 2.59 mmol), in N,N-dimethylformamide (8 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 74 mg (26%) of the desired product as a white solid. MS(ES): (M+1)+ 451.1, 453.1 m/z.

Provenance & Evidence