Benzoic Acid → HCID 22170159, compound

Participants

Reaction Steps

Dissolve [3-(7-chloro-3-methyl-4-oxo-5H-2-oxa-1,5,9-triaza-cyclopenta[a]naphthalen-5-yl)-cyclohexylmethyl]-carbamic acid benzyl ester(70 mg, 0.15 mmol) in dry dichloromethane (5 mL). Add iodotrimethylsilane (0.05 mL, 0.35 mmol) and stir overnight at ambient temperature. Quench with methanol (5 mL) and concentrate in vacuo. Concentrate the resulting residue twice from diethyl ether and use directly without purification. Combine this amine salt with benzoic acid (22 mg, 0.18 mmol), 1-[3-(dimethylamino)-propyl]-3-ethylcarbodiimide hydrochloride (34 mg, 0.18 mmol), 1-hydroxy-7-azabenzo-triazole (24 mg, 0.18 mmol), and N,N-diisopropylethyl amine (0.10 mL, 0.57 mmol) in N,N-dimethylformamide (5 mL) and stir over a weekend at ambient temperature. Concentrate in vacuo and take up in water and extract with ethyl acetate. Dry the combined extracts over sodium sulfate and concentrate in vacuo. Elute the resulting residue over silica gel using ethyl acetate/dichloromethane to give 26 mg (38%) of the desired product as a white solid. MS(ES): (M+1)+ Exact Mass Calc'd: 451.1537. Found: 451.1554 m/z.

Provenance & Evidence