Hydrochloric Acid → Trifluoroacetic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of the title compound from Example 14 Step B in 1,4-dioxane (0.500 mL) was added lithium hydroxide (0.5 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 585.2 [M+H]+; 1H NMR (500 MHz, d6-DMSO) δ 9.09 (d, J=2.0 Hz, 1H), 8.36 (dd, J=8.0, 2.0 Hz, 1H), 8.30 (s, 1H), 8.18 (d, J=7.0 Hz, 1H), 8.14 (t, J=8.0 Hz, 1H), 7.97 (d, J=8.0 Hz, 1H), 7.82 (d, J=8.5 Hz, 1H), 7.75 (dd, J=8.0, 2.0 Hz, 1H), 7.72 (d, J=8.0 Hz, 1H), 7.60 (d, J=8.5 Hz, 1H), 7.47-7.43 (m, 1H), 7.30 (d, J=8.0 Hz, 1H), 7.11 (t, J=7.5 Hz, 1H), 5.34 (s, 2H).

Provenance & Evidence