2-Hydrazinopyridine → HCID 11439953, compound

HRID 733145Notes

Reaction equation

HRID 733145 reaction equation
CN(C)[CH:3]=[CH:4][C:5]([C:7]1[CH:8]=[C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]([F:22])([F:21])[F:20])[CH:10]=[CH:11][CH:12]=1)=O.[NH:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1)[NH2:25]>C(O)C.CCOC(C)=O>[F:20][C:19]([F:21])([F:22])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([C:5]2[CH:4]=[CH:3][N:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=3)[N:25]=2)[CH:8]=1

Participants

5

Reactant 2

HCID 786452-HydrazinopyridineHCID 69073013HCID 69073013, compound

Product 1

HCID 11439953HCID 11439953, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the product from Step 1 (0.224 g, 0.7 mmol) in ethanol (3.5 mL) was added 2-hydrazinopyridine (0.076 g, 0.7 mmol) and the solution was refluxed for 16 hours. The reaction was cooled, diluted with EtOAc, washed with saturated sodium bicarbonate, brine and dried over sodium sulfate. The organic phase was filtered, concentrated, and the crude product was purified by reverse phase HPLC (acetonitrile/water system) (gradient: 30% to 100% acetonitrile over 12 minutes) to give product A (0.033 g, 29% yield, retention time 5.28 minutes) and the regioisomeric product B (0.021 g, 18% yield, retention time 7.25 minutes).

Workup

  1. temperaturethe solution was refluxed for 16 hours
  2. temperatureThe reaction was cooled
  3. washwashed with saturated sodium bicarbonate, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationThe organic phase was filtered
  6. concentrationconcentrated
  7. customthe crude product was purified by reverse phase HPLC (acetonitrile/water system) (gradient: 30% to 100% acetonitrile over 12 minutes)

Sources & evidence

ORD record
ord-490a58e8c4b041aeb49279bcba57fda6
Source dataset
uspto-grants-2009_09
Patent number
US07589116B2

Reaction notes

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