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1,2-Dichloroethane → N-(6-Fluoro-1H-indazol-5-yl)-4-[2-fluoro-4-(trifluoromethyl)phenyl]-1,2-dimethyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide

HRID 734710
Notes
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Reaction equation

HRID 734710 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[CH:12]1[CH2:17][C:16](=[O:18])[N:15]([CH3:19])[C:14]([CH3:20])=[C:13]1[C:21]([OH:23])=O.[NH2:24][C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][C:33]=1[F:34])[NH:30][N:29]=[CH:28]2.C(Cl)CCl.CCN(CC)CC>CN(C=O)C.CCOC(C)=O.Cl>[F:34][C:33]1[CH:32]=[C:31]2[C:27]([CH:28]=[N:29][NH:30]2)=[CH:26][C:25]=1[NH:24][C:21]([C:13]1[CH:12]([C:3]2[CH:4]=[CH:5][C:6]([C:8]([F:10])([F:11])[F:9])=[CH:7][C:2]=2[F:1])[CH2:17][C:16](=[O:18])[N:15]([CH3:19])[C:14]=1[CH3:20])=[O:23]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 450905046-fluoro-1H-indazol-5-amineHCID 690027054-[2-Fluoro-4-(trifluoromethyl)phenyl]-1,2-dimethyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxylic acid

Product 1

HCID 11476792N-(6-Fluoro-1H-indazol-5-yl)-4-[2-fluoro-4-(trifluoromethyl)phenyl]-1,2-dimethyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide
Yield 3%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product of Step 2 (165 mg, 0.498 mmol, 1.00 equiv), 5-amino-6-fluoroindazole (75 mg, 0.498 mmol, 1.0 equiv), and EDC (114 mg, 0.598 mmol, 1.20 equiv) were suspended in 1.0 mL DMF. Et3N (0.083 mL, 0.598 mmol, 1.2 equiv) was added and the solution was stirred at room temperature for 18 hrs. The reaction mixture was diluted with EtOAc and 1N HCl. The phases were separated, and the organic phase was washed twice with 1N HCl, once with satd. NaHCO3, and once with satd. NaCl. The organic phase was dried over Na2SO4, filtered, and concentrated en vacuo. The residue was purified by flash chromatography (0-80% EtOAc in Hexanes) and further purified by reverse-phase HPLC (10-80% CH3CN/H2O, 0.1% TFA over 24 minutes, retention time 15.55 min) to provide 7 mg (3%) of the title compound as a white solid. MS (ES+) m/e 465 [M+H]+

Workup

  1. customThe phases were separated
  2. washthe organic phase was washed twice with 1N HCl, once with satd
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated en vacuo
  6. customThe residue was purified by flash chromatography (0-80% EtOAc in Hexanes)
  7. customfurther purified by reverse-phase HPLC (10-80% CH3CN/H2O, 0.1% TFA over 24 minutes, retention time 15.55 min)

Sources & evidence

ORD record
ord-1274fa04b68d49da83c90d3ada33d50d
Source dataset
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07592357B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes