Chloroform → HCID 86635096, compound

HRID 1696217Notes

Reaction equation

HRID 1696217 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:8][CH2:7][CH2:6][C@H:5]([N:9]2[C:13]3=[C:14]4[CH:20]=[CH:19][NH:18][C:15]4=[N:16][CH:17]=[C:12]3[NH:11][C:10]2=[O:21])[CH2:4]1.C(Cl)(Cl)Cl.C(=O)([O-])O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>ClC(Cl)C>[O:21]=[C:10]1[N:9]([C@H:5]2[CH2:6][CH2:7][CH2:8][C@H:3]([CH:2]=[O:1])[CH2:4]2)[C:13]2=[C:14]3[CH:20]=[CH:19][NH:18][C:15]3=[N:16][CH:17]=[C:12]2[NH:11]1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 67277691HCID 67277691, compound

Product 1

HCID 86635096HCID 86635096, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 1-[trans-3-(hydroxymethyl)cyclohexyl]-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2(1H)-one (180 mg) in dichloroethane (2 ml) was added 1,1,1-tris(acetoxy)-1,1-dihydro-1,2-benziodoxol-3(1H)-one (293 mg) at 4° C. The mixture was stirred at ambient temperature for 2 hours. To the mixture were added chloroform, saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium thiosulfate. The organic layer was separated and extracted with chloroform and washed with water. The extract was dried over MgSO4, filtrated and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel with chloroform:methanol=100:0-85:15 to give trans-3-(2-oxo-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-1(2H)-yl)cyclohexanecarbaldehyde (50 mg).

Workup

  1. customThe organic layer was separated
  2. extractionextracted with chloroform
  3. washwashed with water
  4. dry with materialThe extract was dried over MgSO4
  5. filtrationfiltrated
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel with chloroform

Sources & evidence

ORD record
ord-18dfde571537450f8df487d97a0eb824
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

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