N-(tert-Butyl)-2-isopropoxy-5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)pyrrolo[2,1-f][1,2,4]triazin-2-yl)pyridine-3-sulfonamide → 2-Isopropoxy-5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)pyrrolo[2,1-f][1,2,4]triazin-2-yl)pyridine-3-sulfonamide

Participants

Reaction Steps

N-(tert-Butyl)-2-isopropoxy-5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)pyrrolo[2,1-f][1,2,4]triazin-2-yl)pyridine-3-sulfonamide (0.175 g, 0.306 mmol) in TFA (30 mL) was stirred at RT for 12 h. TFA was removed under reduced pressure and reaction mixture was diluted with 10% NaHCO3 (50 mL). The reaction mixture was extracted with EtOAc (3×30 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to give a residue which was purified by preparative HPLC (Condition B-99 as described in general methods) to afford 2-isopropoxy-5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)pyrrolo[2,1-f][1,2,4]triazin-2-yl)pyridine-3-sulfonamide (65.0 mg, 40.8%) as a white solid. LCMS Condition B-39: retention time 2.32 min, [M+1]=516.2. HPLC Condition B-5: retention time 8.21 min, purity 99.29%. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.42 (d, J=7.1 Hz, 6H), 4.88 (d, J=4.5 Hz, 2H), 5.14 (quintet, J=6.8 Hz, 1H), 6.77 (d, J=3.1 Hz, 1H), 7.08 (s, 2H), 7.24-7.31 (m, 2H), 7.42-7.49 (m, 2H), 7.50-7.62 (m, 4H), 7.77 (td, J=7.7 Hz, J=1.8 Hz, 1H), 7.90 (d, J=2.5 Hz, 1H), 8.42 (dt, J=5.1 Hz, J=1.2 Hz, 1H), 8.65 (d, J=2.5 Hz, 1H), 8.73 (d, J=2.5 Hz, 1H).

Provenance & Evidence