Sodium Thiosulfate → HCID 67278159, compound

HRID 1696259Notes

Reaction equation

HRID 1696259 reaction equation
C([N:3]1[C:11]2[C:6](=[C:7]3[CH:14]=[CH:13][NH:12][C:8]3=[N:9][CH:10]=2)[N:5]([C@H:15]2[CH2:20][CH2:19][CH2:18][CH2:17][C@H:16]2[O:21]C)[C:4]1=[O:23])C.I[Si](C)(C)C.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)([O-])O.[Na+]>C(#N)C>[OH:21][C@@H:16]1[CH2:17][CH2:18][CH2:19][CH2:20][C@@H:15]1[N:5]1[C:6]2=[C:7]3[CH:14]=[CH:13][NH:12][C:8]3=[N:9][CH:10]=[C:11]2[NH:3][C:4]1=[O:23]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 85247Trimethylsilyl iodideHCID 516892Sodium BicarbonateHCID 67278550HCID 67278550, compound

Product 1

HCID 67278159HCID 67278159, compoundYield 162.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of ethyl 1-[(1S,2R)-2-methoxycyclohexyl]-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2(1H)-one (10 mg) in acetonitrile (0.38 mL) was added iodo(trimethyl)silane (0.025 mL) at 5° C. and the mixture was stirred at ambient temperature for 2 hours and further stirred at 60° C. for 2 hours. The mixture was cooled to 4° C. To the mixture were added saturated disodium thiosulfate aqueous solution and saturated aqueous sodium hydrogencarbonate and extracted with chloroform. The organic layer was separated and the aqueous layer was extracted with chloroform. The combined organic layers were dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by preparative Thin layer chromatography (chloroform:methanol=10:1) to give 1-[(1S,2R)-2-hydroxycyclohexyl]-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2(1H)-one (14.1 mg) as a white powder.

Workup

  1. stirringfurther stirred at 60° C. for 2 hours
  2. temperatureThe mixture was cooled to 4° C
  3. extractionextracted with chloroform
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with chloroform
  6. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by preparative Thin layer chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-e03977f578da4811bf32de5415a13dee
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

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