1,2-Dichloroethane → HCID 11487310, compound

HRID 734697Notes

Reaction equation

HRID 734697 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][C:12](=[O:14])[NH:11][C:10]([CH3:15])=[C:9]2[C:16]([OH:18])=O)=[C:4]([F:19])[CH:3]=1.[NH2:20][C:21]1[CH:22]=[C:23]2[C:27](=[C:28]([Cl:30])[CH:29]=1)[NH:26][N:25]=[CH:24]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])[NH:11][C:10]([CH3:15])=[C:9]2[C:16]([NH:20][C:21]2[CH:22]=[C:23]3[C:27](=[C:28]([Cl:30])[CH:29]=2)[NH:26][N:25]=[CH:24]3)=[O:18])=[C:4]([F:19])[CH:3]=1

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 552779967-chloro-1H-indazol-5-amineHCID 688260574-(4-Chloro-2-fluorophenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxylic acid

Product 1

HCID 11487310HCID 11487310, compoundYield 10%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product of Example 3 Step 2 (250 mg, 0.881 mmol, 1.00 equiv), 5-amino-7-chloroindazole (148 mg, 0.881 mmol, 1.0 equiv), and EDC (203 mg, 1.06 mmol, 1.20 equiv) were suspended in 2.0 mL DMF. Et3N (0.148 mL, 1.06 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 38 mg (10%) of the title compound as an off white solid. MS (ES+) m/e 434 [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-620c2fc0e5dc4f6eb1db46e3eb7d0692
Source dataset
uspto-grants-2009_09
Patent number
US07592357B2

Reaction notes

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