HCID 57504489, compound → HCID 57504350, compound

Participants

Reaction Steps

(2S)-2-(1-(5-Chloro-3-(trifluoromethyl)pyridin-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)-3-isopropoxy-N-(5-methylpyridin-2-yl)propanamide (Intermediate K6) (1 g, 0.73 mmol), and 10% Palladium on Carbon (100 mg, 0.09 mmol) in MeOH (25 mL) were stirred under an atmosphere of hydrogen for 16 hours. The reaction mixture was filtered through celite. 10% Palladium on Carbon (100 mg, 0.09 mmol) added and stirred under an atmosphere of hydrogen for a further 16 hours. The reaction mixture was filtered through celite and evaporated. The residue was purified by flash silica chromatography, elution gradient 1 to 5% MeOH in DCM to afford (2S)-3-isopropoxy-N-(5-methylpyridin-2-yl)-2-(1-(3-(trifluoromethyl)pyridin-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)propanamide (0.173 g, 47%). 1H NMR (400 MHz, DMSO) δ 1.08-1.14 (6H, m), 2.24 (3H, s), 3.73-3.79 (1H, m), 3.96-4.05 (2H, m), 5.90 (1H, s), 7.57-7.60 (1H, m), 7.86-7.90 (1H, m), 7.94-7.98 (1H, m), 8.17 (1H, s), 8.55 (1H, s), 8.58-8.61 (1H, m), 8.65 (1H, s), 8.97-9.00 (1H, m), 10.82 (1H, s). m/z (ESI+) (M+H)+=502; HPLC tR=2.30 min.

Provenance & Evidence