HCID 135961971, compound → HCID 135961967, compound
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
Product 1
Reagents, catalysts & solvents 1
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