HCID 136149956, compound → HCID 136149961, compound

HRID 2263408Notes

Reaction equation

HRID 2263408 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[S:14][C:13]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=3)=[N:12][C:11]=2[CH2:25][OH:26])[CH:5]=[CH:4][C:3]=1[C:27]1[NH:31][C:30](=[O:32])[O:29][N:28]=1>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[F:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[C:27]1[NH:31][C:30](=[O:32])[O:29][N:28]=1)[O:8][CH2:9][C:10]1[S:14][C:13]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:22])([F:23])[F:24])=[CH:17][CH:16]=2)=[N:12][C:11]=1[CH:25]=[O:26]

Participants

4

Reactant 1

HCID 136149956HCID 136149956, compound

Product 1

HCID 136149961HCID 136149961, compoundYield 1,004.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

To a mixture of 20 mg of 3-{2-fluoro-4-[4-hydroxymethyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-phenyl}-4H-[1,2,4]oxadiazol-5-one in 10 mL of chloroform was added 23 mg of manganese dioxide. After stirring at room temperature overnight, the reaction mixture was filtered through celite and washed with dichloromethane/methanol. The filtrate was concentrated under reduced pressure to give 200 mg of 5-[3-fluoro-4-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-phenoxymethyl]-2-(4-trifluoromethyl-phenyl)-thiazole-4-carbaldehyde as a beige solid.

Workup

  1. filtrationthe reaction mixture was filtered through celite
  2. washwashed with dichloromethane/methanol
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3cc51b57b6fc4232a6169a7c2a18fed2
Source dataset
uspto-grants-2010_12
Patent number
US07851493B2

Reaction notes

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