Methanol → 2-(3,5-Bis-trifluoromethyl-phenyl)-n-[4-(2-chloro-phenyl)-6-(2-methanesulfonyl-ethylamino)-pyridin-3-yl]-n-methyl-isobutyramide

HRID 1951671Notes

Reaction equation

HRID 1951671 reaction equation
[F:1][C:2]([F:39])([F:38])[C:3]1[CH:4]=[C:5]([C:13]([CH3:37])([CH3:36])[C:14]([N:16]([C:18]2[CH:19]=[N:20][C:21]([NH:31][CH2:32][CH2:33]SC)=[CH:22][C:23]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:30])[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[OH:40][S:41]([O-:44])(=O)=O.OS(O[O-])(=O)=O.OS(O[O-])(=O)=O.[O-]S([O-])(=O)=O.[K+].[K+].[K+].[K+].[K+].[CH3:67]O>>[F:39][C:2]([F:1])([F:38])[C:3]1[CH:4]=[C:5]([C:13]([CH3:37])([CH3:36])[C:14]([N:16]([C:18]2[CH:19]=[N:20][C:21]([NH:31][CH2:32][CH2:33][S:41]([CH3:67])(=[O:44])=[O:40])=[CH:22][C:23]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:30])[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:11])([F:12])[F:10])[CH:8]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 15793144Potassium caroateHCID 873059952-(3,5-Bis-trifluoromethyl-phenyl)-n-[4-(2-chloro-phenyl)-6-(2-methylsulfanyl-ethylamino)-pyridin-3-yl]-n-methyl-isobutyramide

Product 1

HCID 112735842-(3,5-Bis-trifluoromethyl-phenyl)-n-[4-(2-chloro-phenyl)-6-(2-methanesulfonyl-ethylamino)-pyridin-3-yl]-n-methyl-isobutyramideYield 55%

Procedure

A mixture of 50 mg (0.087 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-N-[4-(2-chloro-phenyl)-6-(2-methylsulfanyl-ethylamino)-pyridin-3-yl]-N-methyl-isobutyramide and 130 mg (0.212 mmol) potassium monopersulfate triple salt in 1 ml methanol was stirred at room temperature for 3 days. The reaction was quenched with 1 ml sodium hydrogen sulfite solution 38%. The mixture was treated with 3 ml saturated sodium carbonate solution and extracted with three 5-ml portions of ethyl acetate. The combined organic layers were dried over sodium sulfate, concentrated in vacuo and purified by flash chromatography to give 29 mg (55%) of the title compound as a white foam.

Workup

  1. customThe reaction was quenched with 1 ml sodium hydrogen sulfite solution 38%
  2. additionThe mixture was treated with 3 ml saturated sodium carbonate solution
  3. extractionextracted with three 5-ml portions of ethyl acetate
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. custompurified by flash chromatography

Sources & evidence

ORD record
ord-2d306c283cfa4122857b9c7f5fddf594
Source dataset
uspto-grants-2013_03
Patent number
US08404708B2

Reaction notes

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