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Potassium Carbonate → N-(4-((2-Aminopyridin-4-yl)oxy)-2,5-difluorophenyl)-4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide

HRID 1411156
Notes
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Reaction equation

HRID 1411156 reaction equation
C([NH:4][C:5]1[CH:10]=[C:9]([O:11][C:12]2[C:17]([F:18])=[CH:16][C:15]([NH:19][C:20]([C:22]3[C:23](=[O:38])[N:24]([C:31]4[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=4)[CH:25]=[CH:26][C:27]=3[O:28][CH2:29][CH3:30])=[O:21])=[C:14]([F:39])[CH:13]=2)[CH:8]=[CH:7][N:6]=1)(=O)C.C([O-])([O-])=O.[K+].[K+]>CCO>[NH2:4][C:5]1[CH:10]=[C:9]([O:11][C:12]2[C:17]([F:18])=[CH:16][C:15]([NH:19][C:20]([C:22]3[C:23](=[O:38])[N:24]([C:31]4[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=4)[CH:25]=[CH:26][C:27]=3[O:28][CH2:29][CH3:30])=[O:21])=[C:14]([F:39])[CH:13]=2)[CH:8]=[CH:7][N:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 71566461N-(4-((2-acetamidopyridin-4-yl)oxy)-2,5-difluorophenyl)-4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide

Product 1

HCID 68252797N-(4-((2-Aminopyridin-4-yl)oxy)-2,5-difluorophenyl)-4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamideYield 38%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of Example 1 (1.00 g, 1.86 mmol) and K2CO3 (1.000 g, 7.24 mmol) in EtOH (4 mL) was heated at 120° C. under microwave irradiation for 1 h. The reaction mixture was filtered, washed with EtOH and the filtrate was evaporated to dryness. The crude was stirred in water (15 mL) for a few minutes and collected by filtration. The residue was further purified by successive crystallization from MeOH and MeCN to provide N-(4-((2-aminopyridin-4-yl)oxy)-2,5-difluorophenyl)-4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide (350 mg, 38.0% yield) as a white solid. MS (ESI) m/z: 497.1 (M+H+).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with EtOH
  3. customthe filtrate was evaporated to dryness
  4. filtrationcollected by filtration
  5. customThe residue was further purified by successive crystallization from MeOH and MeCN

Sources & evidence

ORD record
ord-609f8bf7506e46ee81391511ae4bc3cc
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08921565B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes