Triethylamine → HCID 18449083, compound

Participants

Reaction Steps

A solution of methyl 10-(4-cyclohexylbenzoyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-8-carboxylate of Step C (3.38 mmol) in dichloromethane (20 mL) was treated with diphosgene (1.1 equiv.) and triethylamine (1.5 equiv.) and stirred at room temperature overnight. The solvent was then removed in vacuo and the residue was dissolved in dichloromethane (20 mL), and then treated with triethylamine (1.5 equiv) and 1-methylpiperazine (1.5 equiv). The reaction mixture was washed with water, dried over anhydrous magnesium sulfate, filtered and evaporated to dryness. The residue was first chromatographed on silica gel eluting with 2% methanol in dichloromethane, and then chromatographed again eluting with 2% methanol in ethyl acetate to provide the title compound as a white crystalline solid, m.p. 166–168° C. This was converted to the hydrochloride salt by treatment of the free base in anhydrous ethanol with anhydrous hydrogen chloride in dioxane (1.1 equiv.). The salt so obtained was a white crystalline solid, m.p. 203° C. (dec.).

Provenance & Evidence