Trifluoroacetic acid → N-(4-(2-amino-3-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)-2,5-difluorophenyl)-4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide

TFA (1 mL) was added to 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)-4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide (0.17 g, 0.22 mmol) in CH2Cl2 (3 mL) and the mixture was stirred at RT for 1 h. The solvent was removed and the residue was partitioned between satd NaHCO3 solution (30 mL) and EtOAc (30 mL). The aqueous layer was extracted with EtOAc (25 mL) and the combined organics were washed with brine, dried (Na2SO4) and concentrated under reduced pressure to afford N-(4-(2-amino-3-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)-2,5-difluorophenyl)-4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide (120 mg, 95% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 11.12 (s, 1H), 8.24 (t, J=9.8 Hz, 1H), 7.91 (d, J=7.8 Hz, 1H), 7.87 (s, 1H), 7.74 (d, J=5.8 Hz, 1H), 7.58 (s, 1H), 7.47 (m, 2H), 7.36 (t, J=8.7 Hz, 3H), 6.54 (d, J=7.9 Hz, 1H), 5.98 (d, J=5.8 Hz, 1H), 5.69 (s, 2H), 4.27 (q, J=7.0 Hz, 2H), 3.85 (s, 3H), 1.32 (t, J=7.0 Hz, 3H); MS (ESI) m/z: 577.2 (M+H+).

1. customThe solvent was removed
2. customthe residue was partitioned between satd NaHCO3 solution (30 mL) and EtOAc (30 mL)
3. extractionThe aqueous layer was extracted with EtOAc (25 mL)
4. washthe combined organics were washed with brine
5. dry with materialdried (Na2SO4)
6. concentrationconcentrated under reduced pressure

ORD 기록

ord-8b4b6f42b9884e9a94fe984f3b7b8bec

출처 데이터셋

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08569319B2