Ethyl chloroformate → HCID 69122753, compound

Participants

Reaction Conditions

Reaction Steps

A stirred solution of N2-[1-(tetrahydro-2H-pyran-4-yl)-4-piperidinyl]-4-[(2,2,2-trifluoroethyl)oxy]-1,2-benzenediamine (D57, 95 mg, 0.25 mmol) in tetrahydrofuran (5 ml) at room temperature under argon was treated with N,N-diisopropylethylamine (100 mg, 0.78 mmol) followed by ethyl chloroformate (33 mg, 0.30 mmol) and maintained for 3 days. The mixture was concentrated under vacuum and the residue treated with dimethylformamide (5 ml) and heated at 150° C. under argon for 7 hrs. The solution was concentrated under vacuum and the residue treated with 10% Na2CO3 solution and extracted with ethyl acetate. The extract was dried (Na2SO4) and concentrated under vacuum to leave a brown oil, which was purified by Mass-Directed Automated HPLC to afford the title compound as a white solid. This was converted to its HCl salt and isolated as a beige solid (30 mg, 29%).

Provenance & Evidence