Morpholine → HCID 66604368, compound

Participants

Reaction Conditions

Reaction Steps

3-(4-(2-Bromoethoxy)-3-chlorophenyl)-7-(1,1-dioxo-thiomorpholino)-9H-carbazole-1-carboxamide (48.6 mg, 0.076 mmol, Example 408C) was dissolved in DMF (5 ml). Morpholine (0.1 ml, 1.15 mmol) and K2CO3 (40 mg, 0.29 mmol) were added and the mixture heated to 75° C. for 2 hour. The mixture was filtered through a 0.45 um Nylon filter and purified by prep HPLC. Product containing fractions were evaporated to dryness to give 43.0 mg 3-(3-chloro-4-(2-morpholinoethoxy)phenyl)-7-(1,1-dioxo-thiomorpholino)-9H-carbazole-1-carboxamide. MS (ESI) m/e+=583/585, m/e−=581/583 [1 Cl isotope pattern]. HPLC retention time 14.31 min. (Sunfire C18 3.5 μm, 3.0×150 mm column, 15 min gradient, 10-100% B, 0.5 mL/min. Solvent A: 5% CH3CN—95% H2O—0.1% TFA; Solvent B: 95% CH3CN—5% H2O—0.1% TFA), then isocratic at 100% B. 1H NMR (DMSO-d6) δ ppm 11.12 (s, 1H), 8.53 (d, 1H, J=1.2), 8.35 (b, 1H), 8.16 (d, 1H, J=1.5), 8.11 (d, 1H, J=8.8), 7.99 (d, 1H, J=2.3), 7.82 (dd, 1H, J=8.5, 2.2), 7.53 (b, 1H), 7.34 (d, 1H, J=2.0), 7.31 (d, 1H, J=8.8), 7.00 (dd, 1H, J=8.8, 2.2), 4.26 (t, 2H, J=5.8), 3.85 (b, 4H), 3.64-3.59 (m, 4H), 3.23 (b, 4H), 2.79 (t, 2H, J=5.8), 2.58-2.54 (m, 4H).

Provenance & Evidence