Dichloromethane → HCID 58575612, compound

HRID 1807875Notes

Reaction equation

HRID 1807875 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]([C:13]1[CH:14]=[C:15]3[C:20](=[CH:21][C:22]=1[CH3:23])[N:19]1[C:24]([CH:27]([CH:29]4[CH2:31][CH2:30]4)[OH:28])=[N:25][N:26]=[C:18]1[C:17](=[O:32])[NH:16]3)=[O:12])[CH2:6][CH2:5]2.ClCCl.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]([C:13]1[CH:14]=[C:15]3[C:20](=[CH:21][C:22]=1[CH3:23])[N:19]1[C:24]([C:27]([CH:29]4[CH2:31][CH2:30]4)=[O:28])=[N:25][N:26]=[C:18]1[C:17](=[O:32])[NH:16]3)=[O:12])[CH2:6][CH2:5]2

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 46910313HCID 46910313, compound

Product 1

HCID 58575612HCID 58575612, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixed solution of 100 mg of 7-[(5-chloro-2,3-dihydro-1H-indol-1-yl)carbonyl]-1-[cyclopropyl(hydroxy)methyl]-8-methyl[1,2,4]triazolo[4,3-a]quinoxalin-4(5H)-one and 5 mL of dichloromethane was added 113 mg of Dess-Martin periodinane under ice-cooling. The mixed reaction liquid was returned to room temperature, followed by stirring for 4 hours. To the mixed reaction liquid were added a saturated aqueous sodium thiosulfate solution and chloroform, followed by stirring for a while, and then extracting with chloroform, and the organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. Then, the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform/methanol=100/0 to 97/3). To the obtained solid was added 4 mL of methanol to give a mixed solvent, followed by warming and washing. The precipitate was collected by filtration and dried under reduced pressure to obtain 36 mg of 7-[(5-chloro-2,3-dihydro-1H-indol-1-yl)carbonyl]-1-(cyclopropylcarbonyl)-8-methyl[1,2,4]triazolo[4,3-a]quinoxalin-4(5H)-one as a skin-colored solid.

Workup

  1. temperaturecooling
  2. customThe mixed reaction liquid
  3. customwas returned to room temperature
  4. customTo the mixed reaction liquid
  5. stirringby stirring for a while
  6. extractionextracting with chloroform
  7. washthe organic layer was washed with saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThen, the solvent was evaporated under reduced pressure
  10. customThe obtained residue was purified by silica gel column chromatography (chloroform/methanol=100/0 to 97/3)
  11. additionTo the obtained solid was added 4 mL of methanol
  12. customto give a mixed solvent
  13. temperatureby warming
  14. washwashing
  15. filtrationThe precipitate was collected by filtration
  16. customdried under reduced pressure

Sources & evidence

ORD record
ord-e2aacce775b341748e2987c0321f68e8
Source dataset
uspto-grants-2013_01
Patent number
US08357688B2

Reaction notes

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