Pyridine → HCID 67661393, compound

Participants

Reaction Steps

A solution of 118 mg (0.499 mmol) of 2-(4-aminophenyl)ethylcarbamic acid 1,1-dimethylethyl ester (for synthesis see M. H. Fisher, E. R. Parmee, M. R. Mathvink, A. E. Weber, European Patent Application 0 611 003 A1) in 5 mL of dichloromethane was treated with 195.7 mg (0.525 mmol) of 4-(3-octyl-2-imidazolidinon-1-yl)benzenesulfonyl chloride from Example 6 and 40 μL (0.495 mmol) of pyridine. After stirring for 16 h, 1.5 mL of trifluoroacetic acid was added and the reaction mixture stirred for 0.75 h. The volatile components were removed in vacuo. Flash chromatography (silica gel, 5-10% (10% ammonia-methanol)-methylene chloride) afforded 204 mg (86%) of the title compound as a white powder: 1H NMR (400 MHz, CDCl3) δ7.65 (d, 2H, J=9.2 Hz), 7.58 (d, 2H, J=9.2 Hz), 7.03 (d, 2H, J=8.6 Hz), 6.96 (d, 2H, J=8.5 Hz), 3.80-3.76 (m, 2H), 3.50-3.46 (m, 2H), 3.26 (t, 2H, J=7.4 Hz), 2.88 (t, 2H, 6.8 Hz), 2.65 (t, 2H, J=6.9 Hz) 1.65-1.60 (m, 2H), 1.29-1.23 (m, 10H), 0.85 (m, 3H).

Provenance & Evidence