Hydrochloric Acid → Trifluoroacetic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of the title compound from Example 6 Step A (44 mg, 0.07 mmol) in 1,4-dioxane (2 mL) was added lithium hydroxide (1.0 mL, 2.0 M in water, 2.00 mmol), and the resulting mixture was stirred at 50° C. After 2 h, the reaction mixture was rendered acidic by addition of aqueous hydrochloric acid (1.5 mL), then was diluted with 1,4-dioxane and passed though a 0.45 micron syringe filter. Purification by reverse phase HPLC (40 to 100% acetonitrile in water, each with 0.1% v/v TFA) provided the title compound: LCMS m/z 608.9 [M+H]+; 1H NMR (500 MHz, d6-DMSO) δ 8.33 (s, 1H), 8.15 (t, J=8.0 Hz, 1H), 7.99 (d, J=8.0 Hz, 1H), 7.78 (d, J=8.0 Hz, 1H), 7.49 (d, J=8.0 Hz, 1H), 7.45-7.41 (m, 1H), 7.27 (ddd, J=8.0, 8.0, 4JH-F=5.5 Hz, 1H), 7.08 (dd, J=16.5, 8.0 Hz, 4H), 4.95 (s, 2H), 4.56-4.30 (m, 2H), 3.22-3.04 (m, 1H), 2.78-2.68 (m, 1H), 2.68-2.56 (m, 1H), 2.24-1.94 (m, 1H), 1.82-1.62 (br m, 2H), 1.56-1.30 (br m, 2H), 0.82-0.64 (m, 4H).

Provenance & Evidence