p-Toluenesulfonic acid → HCID 136149935, compound

HRID 2263416Notes

Reaction equation

HRID 2263416 reaction equation
[CH3:1][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][O:26]C2CCCCO2)[CH:5]=[CH:4][C:3]=1[C:33]1[NH:37][C:36](=[O:38])[O:35][N:34]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[C:33]1[NH:37][C:36](=[O:38])[O:35][N:34]=1)[O:8][CH2:9][C:10]1[S:14][C:13]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:22])[F:23])=[CH:17][CH:16]=2)=[N:12][C:11]=1[CH:25]=[O:26]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 136149966HCID 136149966, compound

Product 1

HCID 136149935HCID 136149935, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

1.05 g 3-{2-Methyl-4-[4-(tetrahydro-pyran-2-yloxymethyl)-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-phenyl}-4H-[1,2,4]oxadiazol-5-one was suspended in 80 ml methanol. 66.0 mg p-Toluenesulfonic acid were added and the reaction mixture warmed to 60° C. until the reaction mixture became a clear solution. The cooled reaction mixture was evaporated in vacuo. The residue was dissolved in a mixture of 10 ml dimethylformamide and 40 ml dichloromethane. 3.76 g Manganese (IV) oxide on activated charcoil were added and the reaction mixture heated to reflux for two hours. The cooled reaction mixture was filtered through a celite pad. The filtrate was evaporated in vacuo to obtain 670 mg crude 5-[3-methyl-4-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-phenoxymethyl]-2-(4-trifluoromethyl-phenyl)-thiazole-4-carbaldehyde which was used without further purification.

Workup

  1. customThe cooled reaction mixture
  2. customwas evaporated in vacuo
  3. dissolutionThe residue was dissolved in a mixture of 10 ml dimethylformamide and 40 ml dichloromethane
  4. addition3.76 g Manganese (IV) oxide on activated charcoil were added
  5. temperaturethe reaction mixture heated
  6. temperatureto reflux for two hours
  7. customThe cooled reaction mixture
  8. filtrationwas filtered through a celite pad
  9. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-c768d79b776242708e44cbfc30c64504
Source dataset
uspto-grants-2010_12
Patent number
US07851493B2

Reaction notes

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