Dimethylformamide → 10-{[2'-(Cyanomethyl)-1,1'-biphenyl-4-yl]carbonyl}-N-(pyridin-3-ylmethyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide

Participants

Reaction Steps

A mixture of 20 mL of thionyl chloride and 0.243 g (0.001 mol) of 2′-(cyanomethyl)-1,1′-biphenyl-4-carboxylic acid of Step A was heated under reflux for 1 hour. The excess thionyl chloride was removed in vacuo. To the residue was added 35 mL of dry 1,4-dioxane, 0.318 g (0.001 mol) of N-(pyridin-3-ylmethyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide and 0.122 g (0.001 mol) of N,N-dimethylformamide. The reaction was heated under reflux for three hours, cooled and evaporated to dryness. The residue was collected, washed with water and triturated with ether to give 0.62 g. of a tan solid, m.p. 105-108° C.

Provenance & Evidence