HCID 135961971, compound → HCID 135961967, compound

HRID 2233585Notes

Reaction equation

HRID 2233585 reaction equation
Br[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][CH2:26][CH2:27][CH3:28])[CH:5]=[CH:4][C:3]=1[C:29]1[NH:33][C:32](=[O:34])[O:31][N:30]=1.[Cu](C#N)[C:36]#[N:37]>N1C=CC=CC=1>[CH2:25]([C:11]1[N:12]=[C:13]([C:15]2[CH:16]=[CH:17][C:18]([C:21]([F:22])([F:23])[F:24])=[CH:19][CH:20]=2)[S:14][C:10]=1[CH2:9][O:8][C:6]1[CH:5]=[CH:4][C:3]([C:29]2[NH:33][C:32](=[O:34])[O:31][N:30]=2)=[C:2]([CH:7]=1)[C:36]#[N:37])[CH2:26][CH2:27][CH3:28]

Participants

4

Reactant 2

HCID 135961971HCID 135961971, compoundHCID 178418260HCID 178418260, compound

Product 1

HCID 135961967HCID 135961967, compoundYield 10.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
21 °C

Procedure

To a solution of 100 mg of 3-{2-bromo-4-[4-butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-phenyl}-4H-[1,2,4]oxadiazol-5-one in 4 ml of pyridine was added 29 mg of copper cyanide. The resulting mixture was stirred under microwave heating at 21° C. for 10 minutes, then concentrated under reduced pressure. The residue was taken into ethyl acetate, washed with a pH 9 aqueous solution of ammonia, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by preparative thin layer chromatography on silica gel (dichloromethane 95/methanol 5) and precipitated from ethyl acetate/diisopropyl ether/pentane to give 9.5 mg of 5-[4-butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-benzonitrile

Workup

  1. concentrationconcentrated under reduced pressure
  2. washwashed with a pH 9 aqueous solution of ammonia
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by preparative thin layer chromatography on silica gel (dichloromethane 95/methanol 5)
  7. customprecipitated from ethyl acetate/diisopropyl ether/pentane

Sources & evidence

ORD record
ord-ab2b963894a24ce6838395bbc86de923
Source dataset
uspto-grants-2010_05
Patent number
US07709509B2

Reaction notes

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