Sodium Thiosulfate → propane-1-sulfonic acid [2-fluoro-3-(5H-pyrrolo[2,3-b]pyrazine-7-carbonyl)-phenyl]-amide

HRID 1639592Notes

Reaction equation

HRID 1639592 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)=[CH:6][CH:5]=[CH:4][C:3]=1[NH:19][S:20]([CH2:23][CH2:24][CH3:25])(=[O:22])=[O:21].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>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])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:19][S:20]([CH2:23][CH2:24][CH3:25])(=[O:21])=[O:22]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 58001698propane-1-sulfonic acid {2-fluoro-3-[hydroxy-(5H-pyrrolo[2,3-b]pyrazin-7-yl)-methyl]-phenyl}-amide

Product 1

HCID 44538881propane-1-sulfonic acid [2-fluoro-3-(5H-pyrrolo[2,3-b]pyrazine-7-carbonyl)-phenyl]-amideYield 85.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To propane-1-sulfonic acid {2-fluoro-3-[hydroxy-(5H-pyrrolo[2,3-b]pyrazin-7-yl)-methyl]-phenyl}-amide (19, 74 mg, 0.20 mmol) in 1 mL of tetrahydrofuran, Dess-Martin periodane (95 mg, 0.22 mmol) and sodium bicarbonate (200 mg) were added. The reaction was stirred at room temperature for one hour, then poured into saturated aqueous sodium thiosulfate solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography eluting with 70% ethyl acetate in hexane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound (P-0008, 62 mg, 84%). MS (ESI) [M+H+]+=363.1.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under vacuum
  6. customThe resulting material was purified by silica gel column chromatography
  7. washeluting with 70% ethyl acetate in hexane
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-2301be33dace41af8d1e3ee9e9f9f6bc
Source dataset
uspto-grants-2012_02
Patent number
US08110576B2

Reaction notes

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