Trifluoroacetic acid → HCID 136338258, compound

Participants

Reaction Steps

N-(2,6-Difluorophenyl)-3-(2-(dimethylamino)-6-((4-methoxybenzyl)oxy)pyrimidin-4-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-amine (260 mg, 0.443 mmol) in DCM (2.0 mL) was treated with TFA, 99% (2.0 mL, 26.9 mmol) at RT and stirred at 50° for 26 h. The mixture was cooled to RT and evaporated to dryness. The residue was diluted with DCM and extracted with sat'd NaHCO3 solution. The aqueous layer was extracted with DCM 3 times, and the combined organics were dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The crude material was purified with silica gel chromatography (eluting with 0-8% MeOH in DCM with 2 M NH3) to give 6-(5-((2,6-difluorophenyl)amino)-1H-indazol-3-yl)-2-(dimethylamino) pyrimidin-4(3H)-one (85 mg, 0.222 mmol, 50.2% yield) as a yellow solid. MS (ESI, pos. ion) m/z: 383 (M+1); 1H NMR (400 MHz, DMSO-d6) δ ppm 2.90 (s, 6 H), 6.28 (br. s., 1 H), 7.05-7.25 (m, 4 H), 7.45 (d, J=8.80 Hz, 1H), 7.51 (br. s., 1 H), 7.74 (s, 1 H), 10.86 (br. s., 1 H), 13.21 (br. s., 1 H).

Provenance & Evidence