1,2-Dichloroethane → HCID 11430738, compound

HRID 734690Notes

Reaction equation

HRID 734690 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](O)=[O:21].[NH2:23][C:24]1[CH:25]=[C:26]2[C:30](=[C:31]([CH3:33])[CH:32]=1)[NH:29][N:28]=[CH:27]2.C(Cl)CCl.CCN(CC)CC>CN(C=O)C.CCOC(C)=O.Cl>[F:1][C:2]1[CH:7]=[C:6]([C:8]([F:9])([F:10])[F:11])[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]([NH:23][C:24]1[CH:25]=[C:26]2[C:30](=[C:31]([CH3:33])[CH:32]=1)[NH:29][N:28]=[CH:27]2)=[O:21]

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 13820227-methyl-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 11430738HCID 11430738, compoundYield 33.2%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product of Example 21, Step 2 (165 mg, 0.52 mmol, 1.00 equiv), 5-amino-7-methylindazole (77 mg, 0.52 mmol, 1.0 equiv), and EDC (119 mg, 0.624 mmol, 1.20 equiv) were suspended in 1.5 mL DMF. Et3N (0.087 mL, 0.624 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 77 mg (33%) of the title compound as an off white solid. MS (ES+) m/e 447 [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-15ca1a8ba0134bcb9858d177f177fe5a
Source dataset
uspto-grants-2009_09
Patent number
US07592357B2

Reaction notes

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