N,N'-Dimethylethylenediamine → HCID 66930609, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1,1-dimethylethyl 2-(4-bromophenyl)-4,5,7,8-tetrahydropyrazolo[3,4-d]azepine-6(2H)-carboxylate (may be prepared as described in Description 12) (160 mg, 0.41 mmol), 2-oxazolidinone (71 mg, 0.82 mmol), potassium carbonate (170 mg, 1.23 mmol), copper (I) iodide (24 mg, 0.12 mmol) and N,N′-dimethyl-1,2-ethanediamine (13 μl, 0.12 mmol) in dioxane (10 ml) was heated at reflux overnight. The same amounts again of 2-oxazolidinone, copper (I) iodide and N,N′-dimethyl-1,2-ethanediamine were added and the mixture heated for 6 hours. The reaction mixture was transferred to a microwave vial, the same amounts again of 2-oxazolidinone, copper (I) iodide and N,N′-dimethyl-1,2-ethanediamine were added and the mixture heated at 100° C. in microwave for 1 hour. The same amounts again of 2-oxazolidinone, copper (I) iodide and N,N′-dimethyl-1,2-ethanediamine were added and the mixture heated at 100° C. in microwave for a further 2 hours. Crude mixture was filtered through a celite pad washing with methanol. The solvent was evaporated in vacuo, the residue was taken up into ethyl acetate, washed with water and brine, then dried over magnesium sulphate. After evaporation of the solvent in vacuo, the residue was purified by column chromatography on silica gel, eluting with a 50% mixture of ethyl acetate in hexane to afford the title compound (D26). MS (ES+) m/e 343 [M-tBu]+.

Provenance & Evidence