1,2-Dichloroethane → HCID 178429238, compound

HRID 734715Notes

Reaction equation

HRID 734715 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][CH:30]=1)[NH:27][N:26]=[C:25]2[CH3:31].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][CH:30]=2)[NH:27][N:26]=[C:25]3[CH3:31])=[O:19])=[C:4]([F:20])[CH:3]=1

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 68827056HCID 68827056, compoundHCID 178434299HCID 178434299, compound

Product 1

HCID 178429238HCID 178429238, compoundYield 19%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product from Step 2 (130 mg, 0.437 mmol, 1.00 equiv), 5-amino-3-methyl indazole (64 mg, 0.437 mmol, 1.0 equiv), and EDC (100 mg, 0.524 mmol, 1.20 equiv) were suspended in 1.0 mL DMF. Et3N (0.073 mL, 0.524 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 35 mg (19%) of the title compound as a white solid. MS (ES+) m/e 427 [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-ba4f274cebf2437fb19d34fd9beb9121
Source dataset
uspto-grants-2009_09
Patent number
US07592357B2

Reaction notes

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