HCID 59278512, compound → HCID 59278338, compound

HRID 559647Notes

Reaction equation

HRID 559647 reaction equation
[OH:1][CH:2](CO)[CH2:3][C@H:4]([NH:15][C:16]([C:18]1[C:19]2[CH:26]=[N:25][N:24]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[C:20]=2[CH:21]=[N:22][CH:23]=1)=[O:17])[C:5]1[CH:10]=[CH:9][N:8]=[C:7]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:6]=1>CC(C)=O.O>[CH3:14][S:11]([C:7]1[CH:6]=[C:5]([C@@H:4]([NH:15][C:16]([C:18]2[C:19]3[CH:26]=[N:25][N:24]([C:27]4[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=4)[C:20]=3[CH:21]=[N:22][CH:23]=2)=[O:17])[CH2:3][CH:2]=[O:1])[CH:10]=[CH:9][N:8]=1)(=[O:13])=[O:12]

Participants

4

Reactant 1

HCID 59278512HCID 59278512, compound

Product 1

HCID 59278338HCID 59278338, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a room temperature solution of 1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid[(S)-3,4-dihydroxy-1-(2-methanesulfonyl-pyridin-4-yl)-butyl]-amide (0.710 g, 1.42 mmol) in acetone (18 mL) and water (9 mL) was added NaIO4 (608 mg, 2.84 mmol). After 18 hours, the mixture was filtered through diatomaceous earth washing with acetone (3×20 mL). The acetone was removed in vacuo and the aqueous layer was diluted with brine (50 mL) and extracted with EtOAc (3×50 mL). The combined organics layers were dried over magnesium sulfate, filtered, and evaporated to afford 1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid[(S)-1-(2-methanesulfonyl-pyridin-4-yl)-3-oxo-propyl]-amide as white solid which was used without purification.

Workup

  1. filtrationthe mixture was filtered through diatomaceous earth
  2. washwashing with acetone (3×20 mL)
  3. customThe acetone was removed in vacuo
  4. additionthe aqueous layer was diluted with brine (50 mL)
  5. extractionextracted with EtOAc (3×50 mL)
  6. dry with materialThe combined organics layers were dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-e2d7ef383df24160bcb67e22a6acea9e
Source dataset
uspto-grants-2011_11
Patent number
US08063065B2

Reaction notes

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