1,2-Dichloroethane → HCID 11281849, compound

HRID 734716Notes

Reaction equation

HRID 734716 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][C:12](=[O:14])[N:11]([CH3:15])[C:10]([CH3:16])=[C:9]2[C:17]([OH:19])=O)=[C:4]([F:20])[CH:3]=1.[NH2:21][C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][C:30]=1[F:31])[NH:27][N:26]=[CH:25]2.C(Cl)CCl.CCN(CC)CC>CN(C=O)C.CCOC(C)=O.Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][C:12](=[O:14])[N:11]([CH3:15])[C:10]([CH3:16])=[C:9]2[C:17]([NH:21][C:22]2[CH:23]=[C:24]3[C:28](=[CH:29][C:30]=2[F:31])[NH:27][N:26]=[CH:25]3)=[O:19])=[C:4]([F:20])[CH:3]=1

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 450905046-fluoro-1H-indazol-5-amineHCID 68827056HCID 68827056, compound

Product 1

HCID 11281849HCID 11281849, compoundYield 4.5%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product of Example 48, Step 2 (200 mg, 0.672 mmol, 1.00 equiv), 5-amino-6-fluoroindazole (102 mg, 0.672 mmol, 1.0 equiv), and EDC (154 mg, 0.806 mmol, 1.20 equiv) were suspended in 1.5 mL DMF. Et3N (0.112 mL, 0.806 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) to provide 13 mg (4%) of the title compound as a white solid. MS (ES+) m/e 431 [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)

Sources & evidence

ORD record
ord-a97a0d053cb44c128898fb382cf7b1cd
Source dataset
uspto-grants-2009_09
Patent number
US07592357B2

Reaction notes

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