Hydrochloric Acid → Trifluoroacetic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of the title compound from Example 11 Step A (20.0 mg, 0.034 mmol) in 1,4-dioxane (1 mL) was added lithium hydroxide (0.500 mL, 2.0 M in water, 1.00 mmol), and the resulting mixture was stirred at 50° C. After 30 min, the reaction mixture was rendered acidic by addition of aqueous hydrochloric acid, then was diluted with 1,4-dioxane and passed through a 0.45 micron syringe filter. Purification by reverse phase HPLC (50 to 100% acetonitrile in water, each with 0.1% v/v TFA) provided the title compound: LCMS m/z 558.2 [M+H]+; 1H NMR (500 MHz, d6-DMSO) δ 8.29 (s, 1H), 8.15-8.09 (m, 2H), 7.73 (dd, J=8.0, 1.5 Hz, 1H), 7.70 (d, J=7.0 Hz, 1H), 7.42 (t, J=7.5 Hz, 1H), 7.35 (d, J=7.0 Hz, 2H), 7.27 (d, J=8.5 Hz, 1H), 7.23 (d, J=7.0 Hz, 2H), 7.09 (t, J=8.5 Hz, 1H), 5.20 (s, 2H), 2.71-2.66 (m, 1H), 2.11-2.07 (m, 2H), 2.00-1.83 (m, 4H), 1.67-1.60 (m, 2H).

Provenance & Evidence