Sodium Iodide → HCID 17751773, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of the crude 1-{4-[4-amino-7-(2-bromoethyl)pyrrolo[2,1-f][1,2,4]triazin-5-yl]-2-fluorophenyl}-3-[2-fluoro-5-(trifluoromethyl)phenyl]urea (500 mg, crude, 0.31 mmol), morpholine (0.10 ml, 1.12 mmol), triethylamine (0.08 ml, 0.60 mmol) and sodium iodide (7 mg, 0.05 mmol) in 4 ml DMF was heated at 55° C. in a closed vial for 16 h. Cooled to rt, the crude was diluted with 20 ml EtOAc and was washed with aq saturated NaHCO3, brine and dried over Na2SO4. The crude was concentrated and purified via column chromatography (95:5 v/v CH2Cl2-CH3OH) to afford 64 mg of the title compound (yield 47%). 1H-NMR (DMSO-d6 and 1 drop TFA-d) δ 9.44 (d, J=3 Hz, 1H), 9.33 (d, J=3 Hz, 1H), 8.65 (dd, J=7, 2 Hz, 1H, 8.32 (t, J=8 Hz, 1H), 8.15 (s, 1H), 7.55-7.51 (m, 1H), 7.48-7.24 (m, 4H), 6.83 (s, 1H), 4.03-4.01 (m, 2H), 3.69-3.49 (m, 8H), 3.38-3.33 (m, 2H); MS [M+H]+=562.3; LCMS RT=2.84 min.

Provenance & Evidence