Hydrochloric Acid → HCID 57820111, compound

Participants

Reaction Steps

(E)-[2-(3-{4-[(1,1-Dimethyl-2-piperidin-1-yl-ethylamino)-(4-trifluoromethyl-phenylcarbamoyl)-methyl]-phenyl}-acryloylamino)-phenyl]-carbamic acid tert-butyl ester (crude material from Example 15) was treated with 1.25M HCl in methanol (2 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 8 mg desired product (12% over two steps). MS: calc'd 594 (MH+) exp 594 (MH+). 1H NMR (CD3OD, 400 MHz) δ 7.81 (d, 2H, J=10.6 Hz), 7.78 (d, 1H, J=15.6 Hz), 7.71 (d, 2H, J=8.2 Hz), 7.64 (d, 2H, J=10.6 Hz), 7.62 (d, 2H, J=8.2 Hz), 7.32 (m, 4H), 6.90 (d, 1H, J=16 Hz), 4.90 (s, 1H), 3.55 (broad m, 2H), 3.17 (broad m, 2H), 3.16 (d, 1H, J=13.6 Hz), 3.01 (d, 1H, J=13.6 Hz), 2.2-1.8 (m, 6H), 1.33 (s, 3H), 1.32 (s, 3H).

Provenance & Evidence