Sodium Thiosulfate → HCID 57963291, compound

HRID 1690039Notes

Reaction equation

HRID 1690039 reaction equation
[F:1][C:2]1[C:7]([CH:8]([OH:20])[C:9]2[C:17]3[C:16]([O:18][CH3:19])=[N:15][CH:14]=[N:13][C:12]=3[NH:11][CH:10]=2)=[C:6]([F:21])[CH:5]=[CH:4][C:3]=1[NH:22][S:23]([CH2:26][CH2:27][CH3:28])(=[O:25])=[O:24].C(=O)(O)[O-].[Na+].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(OCC)(=O)C.O.O1CCCC1>[F:1][C:2]1[C:7]([C:8]([C:9]2[C:17]3[C:16]([O:18][CH3:19])=[N:15][CH:14]=[N:13][C:12]=3[NH:11][CH:10]=2)=[O:20])=[C:6]([F:21])[CH:5]=[CH:4][C:3]=1[NH:22][S:23]([CH2:26][CH2:27][CH3:28])(=[O:25])=[O:24]

Participants

8

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 57963318HCID 57963318, compound

Product 1

HCID 57963291HCID 57963291, compoundYield 83.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To propane-1-sulfonic acid {2,4-difluoro-3-[hydroxy-(4-methoxy-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methyl]-phenyl}-amide (P-0057, 0.176 g, 0.427 mmol), 9.2 mL of tetrahydrofuran was added followed by sodium bicarbonate (0.358 g, 4.27 mmol) and Dess-Martin periodinane (0.181 g, 0.427 mmol). The reaction was allowed to stir at room temperature for 30 minutes, then 25 mL of saturated sodium thiosulfate and 30 mL of water were added followed by 50 mL of ethyl acetate. The organic layer was dried with magnesium sulfate, filtered, and the filtrate concentrated under vacuum. The resulting residue was purified by silica gel column chromatography eluting with a gradient of 20-60% ethyl acetate in hexanes. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound (P-0058, 146 mg). 1H NMR was consistent with the compound structure. MS(ESI) [M+H+]−=411.1.

Workup

  1. dry with materialThe organic layer was dried with magnesium sulfate
  2. filtrationfiltered
  3. concentrationthe filtrate concentrated under vacuum
  4. customThe resulting residue was purified by silica gel column chromatography
  5. washeluting with a gradient of 20-60% ethyl acetate in hexanes
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-88427ae9f7cf41afac6ee55d9de16303
Source dataset
uspto-grants-2012_04
Patent number
US08153641B2

Reaction notes

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