Trifluoroacetic acid → 2-methoxy-5-(5-phenyl-4-(5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)pyrrolo[2,1-f][1,2,4]triazin-2-yl)pyridine-3-sulfonamide

Participants

Reaction Conditions

Reaction Steps

N-(tert-Butyl)-2-methoxy-5-(5-phenyl-4-(5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)pyrrolo[2,1-f][1,2,4]triazin-2-yl)pyridine-3-sulfonamide (0.180 g, 0.324 mmol) was dissolved in TFA (2.00 mL, 26.0 mmol) and heated at 70° C. for 2 h. The volatile components were removed under reduced pressure and resulting residue was diluted with saturated NaHCO3 (30 mL). The reaction mixture was extracted with EtOAc (3×50 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The resulting residue was purified by preparative HPLC (Condition B-98 as described in general methods) to afford 2-methoxy-5-(5-phenyl-4-(5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)pyrrolo[2,1-f][1,2,4]triazin-2-yl)pyridine-3-sulfonamide (32.0 mg, 19.8%) as off-white solid. LCMS Condition B-22: retention time 1.93 min, [M+1]=500.2. HPLC Condition B-31: retention time 9.01 min, purity 97.4%. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.74 (s, 3H), 4.57 (br s, 2H), 4.89 (br s, 2H), 6.83 (d, J=2.7 Hz, 1H), 7.09 (br s, 2H), 7.26 (dd, J=7.8 Hz, J=4.9 Hz, 1H), 7.37-7.43 (m, 1H), 7.44-7.55 (m, 4H), 7.61 (d, J=6.0 Hz, 1H), 7.99 (d, J=2.8 Hz, 1H), 8.38 (d, J=5.1 Hz, 1H), 8.80 (d, J=2.6 Hz, 1H), 8.96 (d, J=2.5 Hz, 1H).

Provenance & Evidence