Water → Trifluoroacetic acid

Participants

Reaction Steps

(S)-3-(7-(2-(5-Chloro-2-fluorophenyl)pyridin-4-ylamino)-2H-pyrazolo[4,3-b]pyridin-2-yl)propane-1,2-diol TFA salt was dissolved in 600 ml a 1:1 mix of THF and water then added 5 μL of TFA and the reaction mixture was stirred for 2 hours at room temperature before being concentrated to give a residue. The residue was dissolved in DMSO and purified by preparative HPLC using a Sunfire Prep 5 μm C18, 75×30 mm column eluting with a gradient of 10-25% acetonitrile (containing 0.035% TFA) in water (containing 0.05% TFA) to give the title compound as a TFA salt. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.38-3.55 (2H, m) 3.98-4.08 (1H, m) 4.39-4.52 (2H, m) 4.66-4.76 (2H, m) 7.26 (1H, d, J=6.57 Hz) 7.46 (1H, dd, J=10.74, 8.72 Hz) 7.57-7.66 (2H, m) 7.96-8.00 (1H, m) 8.02 (1H, dd, J=6.57, 2.78 Hz) 8.49-8.58 (1H, m) 8.72 (1H, s) 8.73-8.82 (1H, m) 11.34 (1H, s). MS [M+H] found 414.3.

Provenance & Evidence