Hydrochloric Acid → Trifluoroacetic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of the title compound from Example 10 Step E (20.0 mg, 0.035 mmol) in 1,4-dioxane (1.0 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 (40 to 95% acetonitrile in water, each with 0.1% v/v TFA) provided the title compound: LCMS m/z 536.0 [M+H]+; 1H NMR (500 MHz, d6-DMSO) δ 8.30 (s, 1H), 8.14 (d, J=7.5 Hz, 1H), 8.11 (t, J=7.5 Hz, 1H), 7.73-7.70 (m, 2H), 7.43 (t, J=8.0 Hz, 1H), 7.35 (d, J=8.0 Hz, 2H), 7.29-7.26 (m, 3H), 7.09 (t, J=7.5 Hz, 1H), 5.21 (s, 2H), 3.07-3.02 (m, 1H), 2.57 (td, J=14.0, 5.5 Hz, 2 H), 2.26-2.24 (m, 2H), 2.05-2.03 (m, 2H), 1.90-1.82 (m, 2H).

Provenance & Evidence