1,2-Dichloroethane → HCID 11351413, compound

HRID 734689Notes

Reaction equation

HRID 734689 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])[NH:15][C:14]([CH3:19])=[C:13]1[C:20]([OH:22])=O.[NH2:23][C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][C:32]=1[F:33])[NH:29][N:28]=[CH:27]2.C(Cl)CCl.CCN(CC)CC>CN(C=O)C.CCOC(C)=O.Cl>[F:33][C:32]1[CH:31]=[C:30]2[C:26]([CH:27]=[N:28][NH:29]2)=[CH:25][C:24]=1[NH:23][C:20]([C:13]1[CH:12]([C:3]2[CH:4]=[CH:5][C:6]([C:8]([F:9])([F:10])[F:11])=[CH:7][C:2]=2[F:1])[CH2:17][C:16](=[O:18])[NH:15][C:14]=1[CH3:19])=[O:22]

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 450905046-fluoro-1H-indazol-5-amineHCID 688271204-[2-Fluoro-4-(trifluoromethyl)phenyl]-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxylic acid

Product 1

HCID 11351413HCID 11351413, compoundYield 41%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product of Example 21, Step 2 (245 mg, 0.772 mmol, 1.00 equiv), 5-amino-6-fluoroindazole (117 mg, 0.772 mmol, 1.0 equiv), and EDC (177 mg, 0.927 mmol, 1.20 equiv) were suspended in 2.0 mL DMF. Et3N (0.129 mL, 0.927 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 141 mg (41%) of the title compound as an off white solid. MS (ES+) m/e 451 [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-114d2147d7cc47cda41431e2658a29ec
Source dataset
uspto-grants-2009_09
Patent number
US07592357B2

Reaction notes

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