Hydrochloric Acid → HCID 69591910, compound

Participants

Reaction Steps

To a solution of N-(2-pyridin-4-yl-ethyl)-3-{4-[[3-(tetrahydro-pyran-2-yloxy)-benzyl]-(2,4,6-trimethyl-benzenesulfonyl)-amino]-phenyl}-acrylamide (0.059 g, 0.09 mmol) in 0.4 mL methanol and 0.1 mL tetrahydrofuran was added HCl (0.5 mL of a 4.0 M solution in 1,4-dioxane, 2 mmol). The reaction mixture was stirred at room temperature for 24 hr. Saturated aqueous sodium bicarbonate was added and the aqueous solution was washed with methylene chloride. The organic layer was dried (magnesium sulfate) and concentrated. The residue was purified by preparative TLC (eluting with 10% methanol/methylene chloride) to afford 0.018 g of 3-{4-[(3-hydroxy-benzyl)-(2,4,6-trimethyl-benzenesulfonyl)-amino]-phenyl}-N-(2-pyridin-4-yl-ethyl)-acrylamide. 1H NMR (CDCl3) δ 8.32 (d, 2H, J=4.8 Hz), 7.27 (d, 1H, J=16.4 Hz), 7.18 (d, 2H, J=5.2 Hz), 7.03–6.98 (m, 4H), 6.90–6.86 (m, 4H), 6.69 (s, 2H), 6.60 (d, 1H, J=7.2 Hz), 6.24 (d, 1H, J=15.6 Hz), 4.67 (s, 2H), 3.62–3.57 (m, 2H), 2.88 (t, 2H, J=6.4 Hz), 2.41 (s, 6H), 2.24 (s, 3H).

Provenance & Evidence