1-Hydroxybenzotriazole → HCID 10210196, compound

Participants

Reaction Steps

10-(5-Chloro-4-cyclohex-1-en-1-yl-2-methoxybenzoyl)-10,11-dihydro-5H-pyrrolo [2,1-c][1,4]benzodiazepine-3-carboxylic acid of Example 1, Step G (0.200 g, 0.419 mmol), (3-dimethylaminopropyl)methylamine (0.074 mL, 0.503 mmol), 1-hydroxy benzotriazole (0.062 g, 0.461 mmol) and 1-[3-dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.088 g, 0.461 mmol) were combined in amine-free N,N-dimethylformamide (1.7 mL), followed by addition of N,N-diisopropylethyl amine (0.110 mL, 0.629 mmol). The reaction was stirred at room temperature for 12 hours, then diluted with ethyl acetate and washed with water, saturated aqueous sodium bicarbonate and brine. The combined aqueous washings were saturated with sodium chloride and extracted with ethyl acetate. The combined extracts were dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by flash column chromatography on silica gel eluting with 10% methanol in chloroform to provide the title compound (0.220 g) as a white powder, m.p. 116-119° C.

Provenance & Evidence