Hydrogen Peroxide → HCID 86597706, compound

HRID 1951725Notes

Reaction equation

HRID 1951725 reaction equation
[F:1][C:2]([F:45])([F:44])[C:3]1[CH:4]=[C:5]([C:13]([CH3:43])([CH3:42])[C:14]([N:16]([CH3:41])[C:17]2[C:18]([C:33]3[CH:38]=[CH:37][C:36]([F:39])=[CH:35][C:34]=3[CH3:40])=[CH:19][C:20]([N:23]3[CH2:28][CH2:27][CH:26](OC(=S)C)[CH2:25][CH2:24]3)=[N:21][CH:22]=2)=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.OO.[S:48]([O-:51])([OH:50])=[O:49].[Na+]>C(O)(=O)C>[F:11][C:9]([F:10])([F:12])[C:7]1[CH:6]=[C:5]([C:13]([CH3:42])([CH3:43])[C:14]([N:16]([CH3:41])[C:17]2[C:18]([C:33]3[CH:38]=[CH:37][C:36]([F:39])=[CH:35][C:34]=3[CH3:40])=[CH:19][C:20]([N:23]3[CH2:24][CH2:25][CH:26]([S:48]([OH:51])(=[O:50])=[O:49])[CH2:27][CH2:28]3)=[N:21][CH:22]=2)=[O:15])[CH:4]=[C:3]([C:2]([F:45])([F:1])[F:44])[CH:8]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 23665763Sodium BisulfiteHCID 86630728HCID 86630728, compound

Product 1

HCID 86597706HCID 86597706, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of 0.16 g (0.24 mmol) thioacetic acid 5′-{[2-(3,5-bis-trifluoromethyl-phenyl)-2-methyl-propionyl]-methyl-amino}-4′-(4-fluoro-2-methyl-phenyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl ester in 1 ml acetic acid were added 0.12 ml (1.2 mmol) of a 30% aqueous solution of hydrogen peroxide at room temperature. After heating to 60° C., a clear solution was obtained. Stirring was continued at this temperature for 20 h. After cooling to room temperature an aqueous solution of sodium hydrogensulfite was added and the mixture was stirred for 10 min. Acidification with 1 N aqueous hydrochloride solution to pH 1 was followed by extraction with three portions of dichloromethane. The combined organic extracts were dried over sodium sulphate and concentrated. Flash column chromatography gave 0.13 g (83%) of the title compound as a light yellow solid.

Workup

  1. customa clear solution was obtained
  2. additionwas added
  3. stirringthe mixture was stirred for 10 min
  4. extractionAcidification with 1 N aqueous hydrochloride solution to pH 1 was followed by extraction with three portions of dichloromethane
  5. dry with materialThe combined organic extracts were dried over sodium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b1940aec23db4a61911cf1a7b127c900
Source dataset
uspto-grants-2013_03
Patent number
US08404708B2

Reaction notes

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