Sodium Sulfite → HCID 69881514, compound

HRID 352927Notes

Reaction equation

HRID 352927 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([S:11]([N:14]1[CH2:19][CH2:18][N:17]([C:20]([C:22]3[N:27]=[CH:26][C:25]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=4)=[CH:24][N:23]=3)=[O:21])[CH:16]([CH2:34][CH3:35])[CH2:15]1)(=[O:13])=[O:12])=[CH:5]2.ClC1C=CC=C(C(OO)=[O:44])C=1.S([O-])([O-])=O.[Na+].[Na+].C(=O)(O)[O-].[Na+]>C(O)C.C(OCC)C.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([S:11]([N:14]1[CH2:19][CH2:18][N:17]([C:20]([C:22]3[N:27]=[CH:26][C:25]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][N+:29]=4[O-:44])=[CH:24][N:23]=3)=[O:21])[CH:16]([CH2:34][CH3:35])[CH2:15]1)(=[O:13])=[O:12])=[CH:5]2

Participants

7

Reactant 4

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 22710230HCID 22710230, compound

Product 1

HCID 69881514HCID 69881514, compoundYield 18.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 21585056Diethyl ether ethanolSolvent

Procedure

To a methylene chloride solution (50 ml) of 4-[(5-chloroindol-2-yl)sulfonyl]-2-(ethyl)-1-[(5-(pyridin-2-yl)pyrimidin-2-yl]carbonyl]piperazine (234 mg) was added metachloroperbenzoic acid (1.58 g) at room temperature. The resulting mixture was stirred for 5 hours. An aqueous solution (20 ml) of sodium sulfite was added, followed by stirring for 1 hour. To the reaction mixture were added a saturated aqueous solution of sodium bicarbonate and methylene chloride. The water layer was extracted thrice with methylene chloride. The organic layers were combined, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was subjected to chromatography on a silica gel column (methanol:methylene chloride=1:50). The oil thus obtained was solidified from ethanol-diethyl ether, whereby the title compound (44.1 mg) was obtained as a pale yellow solid. MS (FAB) m/z: 527 [(M+H)+, Cl35], 529 [(M+H)+, Cl37].

Workup

  1. stirringby stirring for 1 hour
  2. extractionThe water layer was extracted thrice with methylene chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent
  6. customThe oil thus obtained

Sources & evidence

ORD record
ord-618796b7ead84003b611c12a0254d6a6
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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