Water → HCID 66780847, compound

Participants

Reaction Steps

To a stirred solution of tert-butyl (2R)-2,4-dimethyl-3-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-7-carboxylate (0.75 g, 2.6 mmole) in CH2Cl2 (20 mL) was added trifluoroacetic acid (20 mL). After stirring at RT for 45 min the reaction was concentrated on the rotavap. The residue was redissolved in 4 N HCl in dioxane (50 mL), and the solution was concentrated to dryness. Trituration with Et2O, filtration, and drying under vacuo gave the crude carboxylic acid-hydrochloride salt as a white solid. To a stirred solution of this material in 1:1 DMF/CH2Cl2 (50 mL) was added 1-methyl-2-(methylaminomethyl)indole (0.42 g, 2.6 mmole), Et3N (0.73 mL, 5.2 mmole), HOBt.H2O (0.35 g, 2.6 mmole), and EDC.HCl (0.5 g, 2.6 mmole). After stirring for 18 h the reaction was concentrated on the rotavap, and the residue was taken up in EtOAc (50 mL). The solution was washed sequentially with H2O (50 mL), 1.0 N Na2CO3 (50 mL), and brine (50 mL), then was dried (Na2SO4) and concentrated. Purification by flash chromatography on silica gel (EtOAc) gave the title compound (0.87 g, 86%) as a white solid: MS (ES) m/e 391.2 (M+H)+.

Provenance & Evidence