Hydrochloric Acid → HCID 44158755, compound

Participants

Reaction Steps

(E)-[2-(3-{4-[(4-tert-Butyl-phenylcarbamoyl)-(2-dimethylamino-ethylamino)-methyl]-phenyl}-acryloylamino)-phenyl]-carbamic acid tert-butyl ester (crude material from Example 8) 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 16 mg desired product (24% over two steps). MS: calc'd 514 (MH+) exp 514 (MH+). 1H NMR (CD3OD, 400 MHz) δ 7.79 (d, 1H, J=15.6 Hz), 7.74 (d, 2H, J=8.2 Hz), 7.68 (d, 2H, J=8.2 Hz), 7.49 (d, 2H, J=8.4 Hz), 7.37 (d, 2H, J=8.2 Hz), 7.36 (m, 4H), 6.93 (d, 1H, J=15.6 Hz), 3.40 (t, 2H, J=6.2 Hz), 3.23 (t, 2H, J=6.2 Hz), 2.95 (s, 6H), 1.31 (s, 9H).

Provenance & Evidence