Sodium Hydroxide → 5-[(2,5-Difluorophenyl)[(4-fluorophenyl)sulfonyl]methyl]-4-methyl-N-[3-(methylsulfinyl)propyl]pyridine-2-carboxamide

HRID 1641721Notes

Reaction equation

HRID 1641721 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH:9]([S:25]([C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=1)(=[O:27])=[O:26])[C:10]1[C:11]([CH3:24])=[CH:12][C:13]([C:16]([NH:18][CH2:19][CH2:20][CH2:21][S:22][CH3:23])=[O:17])=[N:14][CH:15]=1.ClC1C=CC=C(C(OO)=[O:43])C=1.[OH-].[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH:9]([S:25]([C:28]1[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=1)(=[O:26])=[O:27])[C:10]1[C:11]([CH3:24])=[CH:12][C:13]([C:16]([NH:18][CH2:19][CH2:20][CH2:21][S:22]([CH3:23])=[O:43])=[O:17])=[N:14][CH:15]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acid2×HCID 577365375-[(2,5-Difluorophenyl)[(4-fluorophenyl)sulfonyl]methyl]-4-methyl-N-[3-(methylthio)propyl]pyridine-2-carboxamide

Product 1

HCID 577365255-[(2,5-Difluorophenyl)[(4-fluorophenyl)sulfonyl]methyl]-4-methyl-N-[3-(methylsulfinyl)propyl]pyridine-2-carboxamideYield 79.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-[(2,5-difluorophenyl)[(4-fluorophenyl)sulfonyl]methyl]-4-methyl-N-[3-(methylthio)propyl]pyridine-2-carboxamide (149 mg, 0.293 mmol) in methylene chloride (5 ml), 3-chloroperbenzoic acid (51 mg, 0.293 mmol) was added under ice cooling, and the mixture was stirred for 30 minutes. 3-Chloroperbenzoic acid (20 mg, 0.116 mmol) was added to the reaction solution under ice cooling, and the resulting mixture was stirred for 15 minutes. 1 N aqueous sodium hydroxide was added to the reaction solution, and the mixture was extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate and filtered, and then the filtrate was concentrated under reduced pressure. The resulting concentration residue was subjected to silica gel column chromatography, and the fraction obtained from an elution with methanol:methylene chloride (=1:30) was concentrated under reduced pressure. Ethylacetate-hexane was added to the resulting concentration residue, and the solid thus precipitated was collected by filtration, to obtain the title compound (122 mg, 0.232 mmol, 79%) as a white powder.

Workup

  1. stirringthe resulting mixture was stirred for 15 minutes
  2. extractionthe mixture was extracted with methylene chloride
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. concentrationThe resulting concentration residue
  7. customthe fraction obtained from an elution with methanol
  8. concentrationmethylene chloride (=1:30) was concentrated under reduced pressure
  9. additionEthylacetate-hexane was added to the resulting concentration residue
  10. customthe solid thus precipitated
  11. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-81da558226764f5db7b7c2ac45cfc6d0
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

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