Sodium Thiosulfate → HCID 22032351, compound

HRID 1792541Notes

Reaction equation

HRID 1792541 reaction equation
O[O:2][S:3]([O-:5])=O.[K+].CS[C:9]1[S:13][C:12]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([C:24]4[C:25]([CH3:48])=[N:26][N:27]([C:29]([C:42]5[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=5)([C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=5)[C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)[CH:28]=4)[CH:22]=3)[N:17]=[CH:16][CH:15]=2)=[CH:11][CH:10]=1.S([O-])([O-])(=O)=S.[Na+].[Na+].[C:56](=O)(O)[O-].[Na+]>O1CCCC1.O.C(OCC)(=O)C>[CH3:56][S:3]([C:9]1[S:13][C:12]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([C:24]4[C:25]([CH3:48])=[N:26][N:27]([C:29]([C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)([C:36]5[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=5)[C:42]5[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=5)[CH:28]=4)[CH:22]=3)[N:17]=[CH:16][CH:15]=2)=[CH:11][CH:10]=1)(=[O:5])=[O:2]

Participants

8

Reactant 4

HCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 22032342HCID 22032342, compoundHCID 23707502Potassium hydroxy sulfite2×

Product 1

HCID 22032351HCID 22032351, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

1 mL aqueous solution of 86 mg oxone was added at room temperature to a solution of 67 mg 4-[5-(methylsulfanyl)-2-thienyl]-6-(3-methyl-1-trityl-1H-4-pyrazolyl)quinoline obtained in Example 155 in tetrahydrofuran, and the mixture was stirred for 1 hour. Further, 60 mg oxone was added thereto and stirred overnight. An aqueous saturated sodium thiosulfate solution was added to the reaction solution, and the mixture was stirred. Then, ethyl acetate, an aqueous saturated sodium bicarbonate solution and water were added thereto, and the organic layer was separated, washed with brine and dried over anhydrous sodium sulfate. The drying agent was filtered off, the filtrate was evaporated, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate), to give 35 mg of the title compound as a pale yellow amorphous.

Workup

  1. stirringstirred overnight
  2. stirringthe mixture was stirred
  3. customthe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe drying agent was filtered off
  7. customthe filtrate was evaporated
  8. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-a36c3c8fa62e43eab30a7845e1565d40
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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