Water → HCID 136149944, compound

HRID 2263428Notes

Reaction equation

HRID 2263428 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH2:10][C:11]2[S:15][C:14]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)=[N:13][C:12]=2[CH2:26][S:27][CH3:28])[CH:6]=[CH:5][C:4]=1[C:29]1[NH:33][C:32](=[O:34])[O:31][N:30]=1.[OH2:35].[OH:36]OS([O-])=O.[K+]>C(#N)C>[CH3:28][S:27]([CH2:26][C:12]1[N:13]=[C:14]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:23])([F:24])[F:25])=[CH:18][CH:17]=2)[S:15][C:11]=1[CH2:10][O:9][C:7]1[CH:6]=[CH:5][C:4]([C:29]2[NH:33][C:32](=[O:34])[O:31][N:30]=2)=[C:3]([O:2][CH3:1])[CH:8]=1)(=[O:36])=[O:35]

Participants

5

Reactant 3

HCID 962Water2×HCID 23707502Potassium hydroxy sulfiteHCID 1354464043-{2-Methoxy-4-[4-methylsulfanylmethyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-phenyl}-4h-1,2,4-oxadiazol-5-one

Product 1

HCID 136149944HCID 136149944, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 35 mg of 3-{2-methoxy-4-[4-methylsulfanylmethyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-phenyl}-4H-1,2,4-oxadiazol-5-one in 4 mL of acetonitrile was added 1 mL of water and 84 mg of Oxone®. The resulting mixture was stirred overnight at room temperature, then poured into water and extracted with dichloromethane. The organic extracts were washed with a saturated aqueous solution if sodium bicarbonate and concentrated under reduced pressure. The crude product was triturated with dichloromethane/methanol/tetrahydrofuran/acetone to give 26 mg of 3-{4-[4-methanesulfonylmethyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-methoxy-phenyl}-4H-1,2,4-oxadiazol-5-one as a white solid.

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic extracts were washed with a saturated aqueous solution if sodium bicarbonate
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was triturated with dichloromethane/methanol/tetrahydrofuran/acetone

Sources & evidence

ORD record
ord-ddfe53d5561c4ed79b21373d26264252
Source dataset
uspto-grants-2010_12
Patent number
US07851493B2

Reaction notes

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