Hydrochloric Acid → HCID 86287760, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of Example 203A (0.062 g, 0.147 mmol) in methanol (1 mL) was treated with hydrogen chloride solution (4 M in 1,4-dioxane, 1 mL, 4 mmol) and heated at 75° C. for 2.5 hours. Additional hydrogen chloride solution (4 M in 1,4-dioxane, 1 mL, 4 mmol) was added and heating was continued for another 3.5 hours. The reaction mixture was then concentrated and the residue was purified by preparative HPLC on a Phenomenex Luna C8(2) 5 μm 100 Å AXIA column (30 mm×75 mm) A gradient of 20-100% acetonitrile (A) and 10 mM ammonium acetate in water (B) was used, at a flow rate of 50 mL/minute (0-0.5 minutes 20% A, 0.5-7.0 minutes linear gradient 20-95% A, 7.0-10.0 minutes 100% A, 10.0-12.0 minutes linear gradient 100-20% A to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ 10.89 (d, J=5.19 Hz, 1H), 8.08 (m, 1H), 7.98 (d, J=8.24 Hz, 1H), 7.89 (s, 1H), 7.47 (m, 1H), 7.42 (s, 1H), 7.34 (d, J=2.14 Hz, 1H), 7.27 (dd, J=8.24, 2.14 Hz, 1H), 6.79 (dd, J=6.71, 5.80 Hz, 1H), 6.76 (d, J=8.24 Hz, 1H), 6.70 (m, 1H), 6.25 (d, J=6.71 Hz, 1H), 4.45 (s, 2H), 4.09 (s, 3H), 2.93 (s, 3H). MS (ESI+) m/z 409.1 (M+H)+.

Provenance & Evidence