Trifluoroacetic acid → HCID 54596615, compound

Participants

Reaction Steps

A solution of N-(4-(2-[bis[(1,1-dimethylethoxy)carbonyl]amino]-3-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)-2,5-difluorophenyl)-5-(4-fluorophenyl)-1-methyl-4-oxo-1,4-dihydropyridine-3-carboxamide (0.115 g, 0.15 mmol) in CH2Cl2 (5 mL) was treated with TFA (0.35 mL, 4.62 mmol) and the solution was stirred at RT for 3 h. The solvent was removed in vacuo and the residue was partitioned between satd NaHCO3 solution (30 mL) and EtOAc (30 mLl). The aqueous layer was extracted with EtOAc (25 mL) and the combined organics were washed with brine, dried (Na2SO4) and concentrated in vacuo to afford N-(4-(2-amino-3-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)-2,5-difluorophenyl)-5-(4-fluorophenyl)-1-methyl-4-oxo-1,4-dihydropyridine-3-carboxamide as off-white solid (82 mg, 97% yield). 1H NMR (400 MHz, DMSO-d6): δ 13.43 (s, 1H), 8.70 (d, J=2.4 Hz, 1H), 8.49 (dd, J=12.6 Hz, 7.3 Hz, 1H), 8.15 (d, J=2.3 Hz, 1H), 7.88 (s, 1H), 7.75 (d, J=5.8 Hz, 1H), 7.69 (m, 2H), 7.59 (d, J=0.8 Hz, 1H), 7.41 (dd, J=11.2 Hz, 7.4 Hz, 1H), 7.27 (t, J=8.9 Hz, 2H), 6.00 (d, J=5.8 Hz, 1H), 5.69 (s, 2H), 3.91 (s, 3H), 3.85 (s, 3H); MS (ESI) m/z: 547.1 (M+H+).

Provenance & Evidence