1-Hydroxybenzotriazole → HCID 10210254, compound

Participants

Reaction Steps

To a solution of 10-{[2-methoxy-2′-chloro[1,1′-biphenyl]-4-yl]carbonyl}-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxylic acid (0.230 g, 0.54 mmol) [prepared from trifluoromethanesulfonic acid 4-formyl-2-methoxy-phenyl ester of Example 7, Step A and 2-chlorophenyl boronic acid, in the manner of Example 7, Steps B–E], in N,N-dimethylformamide (15 mL) is added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.120 g, 0.625 mmol) and 1-hydroxybenzotriazole (0.625 mmol). To the homogeneous solution was added methyl-pyridin-2-ylmethyl-amine (0.625 mmol) and the stirring was continued at room temperature overnight. At the end of this time the solution was poured into water and extracted with ethyl acetate. The combined extracts were washed with water, dried and concentrated and the residue was chromatographed on silica gel, eluting with 95:5 chloroform:methanol. The pure fractions were concentrated, and the residue azeotroped and triturated several times with hexane to yield the title product.

Provenance & Evidence