Sodium Thiosulfate → 2-methyl-propane-1-sulfonic acid [2,4-difluoro-3-(4-methyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-phenyl]-amide

HRID 1187308Notes

Reaction equation

HRID 1187308 reaction equation
[F:1][C:2]1[C:7]([CH:8]([OH:19])[C:9]2[C:17]3[C:16]([CH3:18])=[N:15][CH:14]=[N:13][C:12]=3[NH:11][CH:10]=2)=[C:6]([F:20])[CH:5]=[CH:4][C:3]=1[NH:21][S:22]([CH2:25][CH:26]([CH3:28])[CH3:27])(=[O:24])=[O:23].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>O1CCCC1>[F:1][C:2]1[C:7]([C:8]([C:9]2[C:17]3[C:16]([CH3:18])=[N:15][CH:14]=[N:13][C:12]=3[NH:11][CH:10]=2)=[O:19])=[C:6]([F:20])[CH:5]=[CH:4][C:3]=1[NH:21][S:22]([CH2:25][CH:26]([CH3:28])[CH3:27])(=[O:24])=[O:23]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 583169882-methyl-propane-1-sulfonic acid {2,4-difluoro-3-[hydroxy-(4-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methyl]-phenyl}-amide

Product 1

HCID 532386672-methyl-propane-1-sulfonic acid [2,4-difluoro-3-(4-methyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-phenyl]-amideYield 28.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2-methyl-propane-1-sulfonic acid {2,4-difluoro-3-[hydroxy-(4-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methyl]-phenyl}-amide (77, 99 mg, 0.24 mmol) in 2 mL of tetrahydrofuran, Dess-Martin periodinane (112 mg, 0.265 mmol) is added and the reaction is stirred at room temperature for 2 hours. The reaction is poured into saturated aqueous sodium thiosulfate along with some sodium bicarbonate solid and extracted with ethyl acetate. The organic layer is washed with water, then brine, and dried with sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material is purified by silica gel column chromatography, eluting with ethyl acetate and dichloromethane. Appropriate fractions are combined and concentrated under vacuum to provide the desired compound (P-1003, 28 mg). MS (ESI) [M+H+]+=409.3.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer is washed with water
  3. dry with materialbrine, and dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under vacuum
  6. customThe resulting material is purified by silica gel column chromatography
  7. washeluting with ethyl acetate and dichloromethane
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-970ca070fc4c4ee0a9d859073149811f
Source dataset
uspto-grants-2014_03
Patent number
US08673928B2

Reaction notes

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