Morpholine → HCID 46178248, compound

Participants

Reaction Steps

To a solution of (E)-[2-(3-{4-[1-(4-bromo-phenylcarbamoyl)-4-chloro-butyl]-phenyl}-acryloylamino)-phenyl]-carbamic acid tert-butyl ester (187.5 mg, 0.3 mmol) in DMF (3 mL), morpholine (261 mg, 3 mmol) was added. Then the solution was stirred at 80 degrees Celsius overnight. A solution of 1.25 M HCl/MeOH (4 mL) was added to the residue, the solution was stirred for 4 h at ambient temperature. After reaction, the solution was neutralized with solid NaHCO3. The final product was obtained by preparative HPLC. MS: calc'd 577 (MH+), exp 577 (MH+). 1H NMR (d6-DMSO, 400 MHz), 10.33 (s, 1H), 9.57 (broad s, 2H), 7.61 (d, 1H, J=15.6 Hz), 7.59-7.54 (m, 4H), 7.49-7.46 (m, 4H), 7.36 (d, 1H, J=7.6 Hz), 6.99 (t, 1H, J=7.6 Hz), 6.91-6.84 (m, 2H), 6.71 (broad s, 1H), 3.96 (d, 2H, J=12.0 Hz,), 3.75 (t, 1H, J=7.2 Hz,), 3.62 (t, 2H, J=12.0 Hz), 3.40 (broad s, 2H), 3.14 (t, 2H, J=7.6 Hz), 3.03 (broad s, 2H), 2.09-2.04 (m, 1H), 1.78-1.71 (m, 1H), 1.67-1.57 (m, 2H).

Provenance & Evidence