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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
Notes
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Reaction equation

HRID 1046030 reaction equation
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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 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

Product 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-carboxamideYield 95%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-8b4b6f42b9884e9a94fe984f3b7b8bec
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08569319B2

Reaction notes

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