1,2-Dichloroethane → HCID 11316377, compound

HRID 734702Notes

Reaction equation

HRID 734702 reaction equation
[CH3:1][C:2]1[NH:3][C:4](=[O:21])[CH2:5][CH:6]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=2)[C:7]=1[C:8]([OH:10])=O.[NH2:22][C:23]1[CH:24]=[C:25]2[C:29](=[C:30]([Cl:32])[CH:31]=1)[NH:28][N:27]=[CH:26]2.C(Cl)CCl.CCN(CC)CC>CN(C=O)C.CCOC(C)=O.Cl>[Cl:32][C:30]1[CH:31]=[C:23]([NH:22][C:8]([C:7]2[CH:6]([C:11]3[CH:20]=[CH:19][C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[CH:12]=3)[CH2:5][C:4](=[O:21])[NH:3][C:2]=2[CH3:1])=[O:10])[CH:24]=[C:25]2[C:29]=1[NH:28][N:27]=[CH:26]2

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 160998652-Methyl-4-(2-naphthalenyl)-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxylic acidHCID 552779967-chloro-1H-indazol-5-amine

Product 1

HCID 11316377HCID 11316377, compoundYield 3.3%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product of Example 1, Step 2 (100 mg, 0.355 mmol, 1.00 equiv), 5-amino-7-chloroindazole (59 mg, 0.355 mmol, 1.0 equiv), and EDC (82 mg, 0.427 mmol, 1.20 equiv) were suspended in 1.0 mL DMF. Et3N (0.059 mL, 0.427 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) and further purified by reverse-phase HPLC (10-80% CH3CN/H2O—NH4OH to pH 10 over 9 minutes, retention time 6.18 min) to provide 5 mg (3%) 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 (20-100% EtOAc in Hexanes)
  7. customfurther purified by reverse-phase HPLC (10-80% CH3CN/H2O—NH4OH to pH 10 over 9 minutes, retention time 6.18 min)

Sources & evidence

ORD record
ord-a3d90e9182a4424485f9f1ae9d023f8e
Source dataset
uspto-grants-2009_09
Patent number
US07592357B2

Reaction notes

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