1,1-Dichloroethane → HCID 69732709, compound

Participants

Reaction Steps

To a stirred solution of Example 281 (45 mg) in dichloroethane (10 mL), were added Et3N (0.014 mL) and 4-methylphenyl isocyanate (0.013 mL). Stirring was continued at room temperature over a 2-3 hour period. The solvent was removed under reduced pressure. Crude product was purified by combiflash column chromatography to give the free base of the desired product (27 mg, 50% yield). This material was treated with HCl (4 M) in dioxane and stirred at room temperature overnight. The solvent was removed under reduced pressure to provide the crude product, which was purified by preparative HPLC to provide the title compound. MS [M+H]+573.21, Rf=0.68 (CH2Cl2:MeOH=50:50); H1 NMR (MeOH-d4, δ ppm): 2.25 (s, 3H), 2.85-3.08 (m, 2H), 3.38-3.67 (m, 6H), 4.50 4.54 (m, 1H), 5.45-5.47 (m, 1H), 7.04-7.07 (m, 4H), 7.24 (d, 2H, J=6.3 Hz), 7.40 (dd, 1H, J=6.3 Hz), 7.42-7.45 (m, 2H), 7.63 (t, 1H, J=6.0 Hz), 7.87 (d, 1H, J=6.0 Hz), 7.93 (d, 1H, J=6.0 Hz), 8.10-8.20 (m, 1H), 8.22 (s, 1H), 8.78-8.79 (m, 1H).

Provenance & Evidence