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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

HRID 1046030
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1046030
C(O)(C(F)(F)F)=O.CC(C)(OC([N:14](C(OC(C)(C)C)=O)[C:15]1[C:20]([C:21]2[CH:22]=[N:23][N:24]([CH3:26])[CH:25]=2)=[C:19]([O:27][C:28]2[C:33]([F:34])=[CH:32][C:31]([NH:35][C:36]([C:38]3[C:39](=[O:54])[N:40]([C:47]4[CH:52]=[CH:51][C:50]([F:53])=[CH:49][CH:48]=4)[CH:41]=[CH:42][C:43]=3[O:44][CH2:45][CH3:46])=[O:37])=[C:30]([F:55])[CH:29]=2)[CH:18]=[CH:17][N:16]=1)=O)C>C(Cl)Cl>[NH2:14][C:15]1[C:20]([C:21]2[CH:22]=[N:23][N:24]([CH3:26])[CH:25]=2)=[C:19]([O:27][C:28]2[C:33]([F:34])=[CH:32][C:31]([NH:35][C:36]([C:38]3[C:39](=[O:54])[N:40]([C:47]4[CH:48]=[CH:49][C:50]([F:53])=[CH:51][CH:52]=4)[CH:41]=[CH:42][C:43]=3[O:44][CH2:45][CH3:46])=[O:37])=[C:30]([F:55])[CH:29]=2)[CH:18]=[CH:17][N:16]=1
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Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 68009418N-(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

Produkt 1

HCID 54596614N-(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-carboxamideAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

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+).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-8b4b6f42b9884e9a94fe984f3b7b8bec
Quelldatensatz
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08569319B2

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