Water → HCID 59278212, compound

HRID 1698172Notes

Reaction equation

HRID 1698172 reaction equation
[CH3:1][S:2][C:3]1[O:4][C:5]([C@@H:8]([NH:11][C:12]([C:14]2[C:15]3[CH:22]=[N:21][N:20]([C:23]4[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=4)[C:16]=3[CH:17]=[N:18][CH:19]=2)=[O:13])[CH2:9][CH3:10])=[CH:6][N:7]=1.I([O-])(=O)(=O)=[O:31].[Na+].[OH2:36]>C(#N)C.[Ru](Cl)(Cl)Cl>[CH3:1][S:2]([C:3]1[O:4][C:5]([C@@H:8]([NH:11][C:12]([C:14]2[C:15]3[CH:22]=[N:21][N:20]([C:23]4[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=4)[C:16]=3[CH:17]=[N:18][CH:19]=2)=[O:13])[CH2:9][CH3:10])=[CH:6][N:7]=1)(=[O:31])=[O:36]

Participants

6

Reactant 3

HCID 962WaterHCID 23667635Sodium periodateHCID 45137857HCID 45137857, compound

Product 1

HCID 59278212HCID 59278212, compound

Reagents, catalysts & solvents 2

HCID 61850Ruthenium trichlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid [(S)-1-(2-methylsulfanyl-oxazol-5-yl)-propyl]amide (0.1 g, 0.2 mmol) in a mixture of acetonitrile (25 mL) and water (5 mL) was added sodium periodate (0.155 g, 0.725 mmol) followed by ruthenium trichloride (5 mg, 0.02 mmol). After 6 hours, the mixture was filtered and the filtrate was diluted with water (50 mL) and extracted with ethyl acetate (3×50 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated. The crude material was dissolved in ethyl acetate and passed through a pad of silica. The material from the pad was crystallized from ethyl acetate-hexanes to afford the title compound.

Workup

  1. filtrationthe mixture was filtered
  2. additionthe filtrate was diluted with water (50 mL)
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe crude material was dissolved in ethyl acetate
  8. customThe material from the pad was crystallized from ethyl acetate-hexanes

Sources & evidence

ORD record
ord-b0a67156927a4a21a4e3c1e1bd07f823
Source dataset
uspto-grants-2012_04
Patent number
US08163918B2

Reaction notes

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