Tetrahydrofuran → HCID 86659280, compound

HRID 2362637Notes

Reaction equation

HRID 2362637 reaction equation
[Cl:1][C:2]1[C:3]([C:31]2[S:35][C:34]([C:36]3([O:40][CH2:41][O:42][CH3:43])[CH2:39][CH2:38][CH2:37]3)=[N:33][CH:32]=2)=[C:4]2[CH:10]=[C:9]([C:11]3[CH:12]=[N:13][N:14]([CH2:16][CH:17]([OH:20])CO)[CH:15]=3)[N:8]([S:21]([C:24]3[CH:30]=[CH:29][C:27]([CH3:28])=[CH:26][CH:25]=3)(=[O:23])=[O:22])[C:5]2=[N:6][CH:7]=1.O1CCCC1.I([O-])(=O)(=O)=O.[Na+]>O>[Cl:1][C:2]1[C:3]([C:31]2[S:35][C:34]([C:36]3([O:40][CH2:41][O:42][CH3:43])[CH2:37][CH2:38][CH2:39]3)=[N:33][CH:32]=2)=[C:4]2[CH:10]=[C:9]([C:11]3[CH:12]=[N:13][N:14]([CH2:16][CH:17]=[O:20])[CH:15]=3)[N:8]([S:21]([C:24]3[CH:30]=[CH:29][C:27]([CH3:28])=[CH:26][CH:25]=3)(=[O:23])=[O:22])[C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 23667635Sodium periodateHCID 67003853HCID 67003853, compound

Product 1

HCID 86659280HCID 86659280, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an ambient solution of 3-(4-(5-chloro-4-(2-(1-(methoxymethoxy)cyclobutyl)thiazol-5-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-1H-pyrazol-1-yl)propane-1,2-diol (Example 14B) (1.28 g, 1.987 mmol) in a solvent mixture of tetrahydrofuran (14.90 mL) and water (4.97 mL) was added solid sodium periodate (0.638 g, 2.98 mmol) in a single portion. The reaction was stirred at room temperature for 1 hour and was then quenched by the addition of 10% aqueous sodium thiosulfate solution (10 mL) and ethyl acetate (15 mL). The layers were separated, and the aqueous layer was extracted with additional ethyl acetate (2×15 mL). The combined organics were washed once with 10% aqueous sodium thiosulfate solution (10 mL), dried with anhydrous sodium sulfate, filtered and concentrated to give the title compound, which was used in the next step without further purification. MS ESI(−) m/z 610.2 [M−H]−.

Workup

  1. customwas then quenched by the addition of 10% aqueous sodium thiosulfate solution (10 mL) and ethyl acetate (15 mL)
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with additional ethyl acetate (2×15 mL)
  4. washThe combined organics were washed once with 10% aqueous sodium thiosulfate solution (10 mL)
  5. dry with materialdried with anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c57e20d81a31456f94bced507eb15b8e
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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