1-Hydroxybenzotriazole → HCID 22053644, compound

Participants

Reaction Steps

To a stirred solution of the 10-[(2′,6-dichloro-3-methoxy-[1,1′-biphenyl]-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine carboxylic acid of Step C (0.250 g, 0.49 mmol) in N,N-dimethylformamide (2 mL) was added 3-(methylaminomethyl) pyridine (0,073 g, 0.59 mmol), 1-hydroxybenzotriazole (0.074 g, 0.54 mmol), 1-[3-(dimethylamino)propyl]-3-ethyl carbodiimide hydrochloride (0.093 g, 0.54 mmol), and N,N-diisopropylethyl amine (0.096 g, 0.74 mmol). After stirring overnight, the reaction mixture was taken up in chloroform, washed with saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, filtered and evaporated to dryness. Trituration of the residue with ethyl acetate provided the title compound (0.225 g) as a white solid, m.p. 196–198° C., found to be 93.88% pure by analytical HPLC [Primesphere C-18 column (2.0×150 mm); mobile phase: 45/55 acetonitrile/water containing 0.1% phosphoric acid].

Provenance & Evidence