Dichloromethane → HCID 9828829, compound

Participants

Reaction Steps

To a solution of the aniline of Example 1 (50 mg, 1.15 mmol) in dichloromethane (5 ml) at RT was added DMAP (cat.) and ethyl isocyanate (100 μl, 1.1 eq) and the mixture stirred at this temperature overnight. The reaction mixture was concentrated in vacuo to yield a yellow foam, which was subjected to column chromatography (SiO2 ; ethyl acetate) to afford the free base of the title compound (445 mg, 77%) as a white foam. The material was converted to its hydrochloride salt (Found: C, 68.89, H, 6.38; N, 7.81. C32H33N3O3. HCl. 0.75 H2O requires C, 68.93; H, 6.42; N, 7.54%). δH (d4MeOH) 1.12 (3H, m), 2.96-3.30 (8H, m), 3.71 (3H, s), 4.36 (1H, t, J 8.0 Hz), 5.13 (1H, m), 6.87 (4H, m), 7.02 (1H, d, J 7.5 Hz), 7.11-7.16 (5H, m), 7.52 (1H, s), 7.83 (2H, br), and 8.58 (2H, br). m/z ESI 508 (MH+, 100%), 530 (MNa+, 3).

Provenance & Evidence