Triacetoxyperiodinane → propane-1-sulfonic acid [2,4-difluoro-3-(5H-pyrrolo[2,3-b]pyrazine-7-carbonyl)-phenyl]-amide

HRID 1639581Notes

Reaction equation

HRID 1639581 reaction equation
[F:1][C:2]1[C:7]([CH:8]([OH:18])[C:9]2[C:17]3[C:12](=[N:13][CH:14]=[CH:15][N:16]=3)[NH:11][CH:10]=2)=[C:6]([F:19])[CH:5]=[CH:4][C:3]=1[NH:20][S:21]([CH2:24][CH2:25][CH3:26])(=[O:23])=[O:22].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>O1CCCC1>[F:1][C:2]1[C:7]([C:8]([C:9]2[C:17]3[C:12](=[N:13][CH:14]=[CH:15][N:16]=3)[NH:11][CH:10]=2)=[O:18])=[C:6]([F:19])[CH:5]=[CH:4][C:3]=1[NH:20][S:21]([CH2:24][CH2:25][CH3:26])(=[O:23])=[O:22]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 58001696propane-1-sulfonic acid 2,4-difluoro-3-[hydroxy-(5H-pyrrolo[2,3-b]pyrazin-7-yl)-methyl]-phenyl-amide

Product 1

HCID 44512442propane-1-sulfonic acid [2,4-difluoro-3-(5H-pyrrolo[2,3-b]pyrazine-7-carbonyl)-phenyl]-amideYield 77.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To propane-1-sulfonic acid 2,4-difluoro-3-[hydroxy-(5H-pyrrolo[2,3-b]pyrazin-7-yl)-methyl]-phenyl-amide (9, 0.243 g, 0.635 mmol), 15 mL of tetrahydrofuran was added, followed by Dess-Martin periodinane (0.270 g, 0.635 mmol). The reaction was allowed to stir at room temperature for 15 minutes, then extracted with ethyl acetate and 5:1 saturated sodium bicarbonate:saturated sodium thiosulfate. The organic layer was dried with anhydrous magnesium sulfate, filtered, and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography eluting with a gradient of 1 to 5% methanol in dichloromethane. The resulting material was re-purified by silica gel column chromatography eluting with a gradient of 10 to 80% ethyl acetate in hexanes. Appropriate fractions were combined and concentrated under vacuum to give the desired compound (P-0001, 188 mg). MS (ESI)[M+H+]+=381.0.

Workup

  1. extractionextracted with ethyl acetate and 5:1 saturated sodium bicarbonate
  2. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under vacuum
  5. customThe resulting material was purified by silica gel column chromatography
  6. washeluting with a gradient of 1 to 5% methanol in dichloromethane
  7. customThe resulting material was re-purified by silica gel column chromatography
  8. washeluting with a gradient of 10 to 80% ethyl acetate in hexanes
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-4234c94519e6463a87e11b6797ca5ef9
Source dataset
uspto-grants-2012_02
Patent number
US08110576B2

Reaction notes

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