Potassium Carbonate → HCID 44512046, compound

HRID 1690018Notes

Reaction equation

HRID 1690018 reaction equation
[F:1][C:2]1[C:7]([CH:8]([OH:18])[C:9]2[C:17]3[CH:16]=[N:15][CH:14]=[N:13][C:12]=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.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[F:1][C:2]1[C:7]([C:8]([C:9]2[C:17]3[CH:16]=[N:15][CH:14]=[N:13][C:12]=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 11430Potassium CarbonateHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 57963310HCID 57963310, compound

Product 1

HCID 44512046HCID 44512046, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To propane-1-sulfonic acid {2-fluoro-3-[hydroxy-(7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methyl]-phenyl}-amide (P-0005, 79 mg, 0.22 mmol) in 1 mL of tetrahydrofuran, Dess-Martin periodane (101 mg, 0.24 mmol) was added. The reaction was stirred at room temperature for one hour. The reaction was poured into sodium thiosulfate and potassium carbonate solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under vacuum and purified by silica gel column chromatography eluting with 5% methanol in dichloromethane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound (P-0006, 75 mg, 95%). 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 was concentrated under vacuum
  6. custompurified by silica gel column chromatography
  7. washeluting with 5% methanol in dichloromethane
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-218bc58c69c84b178560d308eab52e77
Source dataset
uspto-grants-2012_04
Patent number
US08153641B2

Reaction notes

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