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

HRID 734681
Notes
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Reaction equation

HRID 734681 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][C:13](=[O:15])[NH:12][C:11]([CH3:16])=[C:10]2[C:17](O)=[O:18])=[CH:5][CH:4]=1.[NH2:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][C:31]=1[F:32])[NH:28][N:27]=[CH:26]2.C(Cl)CCl.CCN(CC)CC>CN(C=O)C.CCOC(C)=O.Cl>[F:32][C:31]1[CH:30]=[C:29]2[C:25]([CH:26]=[N:27][NH:28]2)=[CH:24][C:23]=1[NH:22][C:17]([C:10]1[CH:9]([C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:21])([F:20])[F:1])=[CH:8][CH:7]=2)[CH2:14][C:13](=[O:15])[NH:12][C:11]=1[CH3:16])=[O:18]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 160998632-Methyl-6-oxo-4-(4-(trifluoromethyl)phenyl)-1,4,5,6-tetrahydropyridine-3-carboxylic acidHCID 450905046-fluoro-1H-indazol-5-amine

Product 1

HCID 113738464-(4-(trifluoromethyl)phenyl)-N-(6-fluoro-1H-indazol-5-yl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide
Yield 22.4%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product of Example 5, Step 2 (200 mg, 0.67 mmol, 1.00 equiv), 5-amino-6-fluoroindazole (101 mg, 0.67 mmol, 1.0 equiv), and EDC (153 mg, 0.80 mmol, 1.20 equiv) were suspended in 2.0 mL DMF. Et3N (0.112 mL, 0.80 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 (20-100% EtOAc in Hexanes) to provide 65 mg (22%) of the title compound as an off white solid. MS (ES+) m/e 433 [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 (20-100% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-df542294df854277afd387230fd386b9
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