Reaction Steps
A solution of methyl 4-ethoxyphenyldithiocarbamate (0.0274 g, 0.121 mmol) in DMF (0.2 mL) was added to a mixture of 3-amino-N,N-diethyl-4-(isopentylamino)benzamide (0.0334 g, 0.120 mmol) and red mercury(II) oxide (0.0261 g, 0.121 mmol) in DMF (0.2 mL). The resulting suspension was stirred vigorously for 5.5 h, and an additional portion of red mercury(II) oxide (0.0130 g, 0.0600 mmol) was added. After stirring an additional 16 h, the reaction was diluted with 9:1 CH2Cl2:MeOH, loaded onto a small plug of silica gel, and eluted with the same solvent system. The eluant was concentrated, and the residue was purified by reverse phase HPLC (gradient 20–70% CH3CN in H2O) to provide the title compound (0.0287 g, 45%) as its TFA salt. This material was lyophilized from H2O/dioxane to produce a white solid. 1H-NMR (CD3OD): δ 7.60 (d, J=8.4 Hz, 1H), 7.44–7.38 (2 overlapping d; 3H), 7.35 (s, 1H), 7.11 (d, J=9.2 Hz, 2H), 4.32 (br t, J=7.2 Hz, 2H), 4.12 (q, J=7.6 Hz, 2H), 3.56 (br s, 2H), 3.32 (br s, 2H), 1.85–1.76 (br m, 3H), 1.43 (t, 7.6 Hz, 3H), 1.25 (br s, 3H), 1.14 (br s, 3H), 1.08 (d, J=6.4 Hz, 6H). 13C-NMR(CD3OD): δ 172.51, 160.57, 151.15, 134.20, 132.87, 130.29, 128.70, 128.44, 123.46, 117.18, 111.54, 111.23, 65.02, 45.07, 43.16, 41.13, 37.49, 27.26, 22.76, 15.07, 14.35, 13.07. Anal. Calcd for MS (ESI) (M+H)+=423.
