Hydrochloric Acid → (E)-N-(2-Amino-phenyl)-3-{4-[(2-morpholin-4-yl-ethoxy)-(4-trifluoromethyl-phenylcarbamoyl)-methyl]-phenyl}-acrylamide

Participants

Reaction Steps

(E)-[2-(3-{4-[(2-Morpholin-4-yl-ethoxy)-(4-trifluoromethyl-phenylcarbamoyl)-methyl]-phenyl}-acryloylamino)-phenyl]-carbamic acid tert-butyl ester (118 mg, 0.177 mmol) was treated with 1.25M HCl in methanol (1 mL) at room temperature for 2 hours. The reaction was quenched slowly with solid sodium bicarbonate until the pH was 6-7. The mixture was diluted in acetonitrile with a small amount of dimethylsulfoxide, passed through a 40 μm pipette filter, and then purified by preparative HPLC to obtain 17 mg desired product (17%). MS: calc'd 569 (MH+) exp 569 (MH+). 1H NMR (d6-DMSO, 400 MHz) δ 10.6 (s, 1H, rotamer a), 10.4 (s, 1H, rotamer b), 9.43 (s, 1H), 7.91 (d, 2H, J=8.0 Hz), 7.70 (d, 2H, J=8.8 Hz), 7.65 (d, 2H, J=8.0 Hz), 7.58 (d, 2H, J=8.8 Hz), 7.55 (d, 1H, J=15.6 Hz), 7.34 (d, 1H, J=6.4 Hz), 6.92 (d, 1H, J=15.6 Hz), 6.91 (t, 1H, J=6.4 Hz), 6.75 (d, 1H, J=7.4 Hz), 6.57 (t, 1H, J=7.4 Hz), 5.11 (s, 1H), 4.96 (s, 2H), 3.70 (broad m, 4H), 3.55 (broad m, 2H), 2.70-2.35 (broad m, 6H).

Provenance & Evidence