Sodium Thiosulfate → HCID 21922657, compound

HRID 1245008Notes

Reaction equation

HRID 1245008 reaction equation
Cl[C:2]1C=CC=C(C(OO)=O)C=1.[CH2:12]([N:19]1[CH2:24][CH2:23][CH:22]([N:25]2[CH:29]=[CH:28][C:27]([C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=3)=[C:26]2[C:37]2[CH:42]=[CH:41][N:40]=[C:39](SC)[N:38]=2)[CH2:21][CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[S:45]([O-:49])([O-])(=[O:47])=S.[Na+].[Na+]>C(OCC)(=O)C>[CH2:12]([N:19]1[CH2:24][CH2:23][CH:22]([N:25]2[CH:29]=[CH:28][C:27]([C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=3)=[C:26]2[C:37]2[CH:42]=[CH:41][N:40]=[C:39]([S:45]([CH3:2])(=[O:49])=[O:47])[N:38]=2)[CH2:21][CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 21922646HCID 21922646, compound

Product 1

HCID 21922657HCID 21922657, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3.51 g (15.26 mmol) of 69–75 wt. % of m-chloroperbenzoic acid were added in small portions to a solution of 3.50 g (7.63 mmol) of 1-(1-benzylpiperidin-4-yl)-3-(4-fluorophenyl)-2-(2-methylthiopyrimidin-4-yl)-1H-pyrrole [prepared as described in step 42(i) above] in 35 ml of ethyl acetate with ice-cooling. The resulting mixture was stirred at room temperature 2 days, after which a 10% aqueous solution of sodium thiosulfate was added to the reaction mixture followed by extraction with ethyl acetate. The organic extract was washed with water and then concentrated by evaporation under reduced pressure. The residue thus obtained was purified by chromatography on a silica gel column using a 9:1 by volume mixture of dichloromethane and methanol as the eluant to give 2.48 g (yield 66%) of the title compound as a pale brown amorphous solid.

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with water
  5. concentrationconcentrated by evaporation under reduced pressure
  6. customThe residue thus obtained
  7. customwas purified by chromatography on a silica gel column
  8. additionby volume mixture of dichloromethane and methanol as the eluant

Sources & evidence

ORD record
ord-66482e21ebac4470b68d482e906a0d6a
Source dataset
uspto-grants-2006_10
Patent number
US07122666B2

Reaction notes

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