Metaperiodic acid → HCID 178449202, compound

HRID 2280418Notes

Reaction equation

HRID 2280418 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([NH:13]/[C:14](/[NH:26][CH2:27][CH:28]([CH3:30])[CH3:29])=[N:15]\[C:16](=[O:25])[C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([S:23][CH3:24])[CH:18]=3)[NH:10][N:9]=2)=[CH:4][CH:3]=1.I(O)(=O)(=O)=[O:32]>CC(C)=O.C(#N)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([NH:13]/[C:14](/[NH:26][CH2:27][CH:28]([CH3:30])[CH3:29])=[N:15]\[C:16](=[O:25])[C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([S:23]([CH3:24])=[O:32])[CH:18]=3)[NH:10][N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 65185Metaperiodic acidHCID 178503169HCID 178503169, compound

Product 1

HCID 178449202HCID 178449202, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 21918305Acetone acetonitrileSolvent

Procedure

To an orange solution of (Z)—N-[[[3-(4-fluorophenyl)-1H-pyrazol-5-yl]amino]-(isobutylamino)methylene]-3-methylsulfanyl-benzamide (500 mg, 1.175 mmol) and ferric chloride trihydrate (9.5 mg, 0.035 mmol) in acetone:acetonitrile (1:1) was added periodic acid (295 mg, 1.3 mmol) in one portion. After stirring the resulting mixture at room temperature for ca. 21 hr, the reaction was quenched by adding aqueous sodium thiosulfate. The product was extracted with DCM, and the organic layer was washed with brine and dried over MgSO4. The drying reagent was removed by filtration, and the filtrate was concentrated onto silica gel and purified by silica chromatography (50-90% EtOAc in hexanes) to provide the title compound (77% yield). MS (EI+) m/z: 442.17.

Workup

  1. customthe reaction was quenched
  2. additionby adding aqueous sodium thiosulfate
  3. extractionThe product was extracted with DCM
  4. washthe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. customThe drying reagent was removed by filtration
  7. concentrationthe filtrate was concentrated onto silica gel
  8. custompurified by silica chromatography (50-90% EtOAc in hexanes)

Sources & evidence

ORD record
ord-3d21b1c1428a404295d9d3e12d851603
Source dataset
uspto-grants-2015_09
Patent number
US09139532B2

Reaction notes

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