Trifluoroacetic acid → HCID 22933491, compound

HRID 1269970Notes

Reaction equation

HRID 1269970 reaction equation
FC(F)(F)C(O)=O.O1CCCCC1[N:14]1[C:22]2[CH:21]=[CH:20][C:19]([O:23]C3CCCCO3)=[C:18]([C:30]#[N:31])[C:17]=2[CH:16]=[N:15]1.C(=O)([O-])O.[Na+]>ClCCl.C(OCC)(=O)C>[OH:23][C:19]1[CH:20]=[CH:21][C:22]2[NH:14][N:15]=[CH:16][C:17]=2[C:18]=1[C:30]#[N:31]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 69432236HCID 69432236, compound

Product 1

HCID 22933491HCID 22933491, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Trifluoroacetic acid (1.5 ml) was added dropwise to a solution of 1-tetrahydro-2H-pyran-2-yl-5-(tetrahydro-2H-pyran-2-yloxy)-1H-indazole-4-carbonitrile (227 mg, 0.693 mmol) in dichloromethane (6.5 ml) at room temperature, and the resulting mixture was stirred for 1.5 hours while being maintained at room temperature. The reaction solution was diluted with ethyl acetate and adjusted to pH 7 with a saturated aqueous sodium hydrogencarbonate solution, followed by partition and extraction. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then filtered, and the filtrate was concentrated under reduced pressure to obtain a crude product. The crude product was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain 5-hydroxy-1H-indazole-4-carbonitrile (108 mg, 98%).

Workup

  1. customby partition
  2. extractionextraction
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customto obtain a crude product
  8. customThe crude product was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-0c37eb47b45a4e97b6fae371bd365398
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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