Water → HCID 178482468, compound

HRID 1620470Notes

Reaction equation

HRID 1620470 reaction equation
Cl.Cl.[CH3:3][NH:4][C:5]1=[N:6][C:7](=[O:17])[S:8]/[C:9]/1=[CH:10]\[CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.C(=O)([O-])[O-].[Cs+].[Cs+].F[C:25]1[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][C:26]=1[C:33]([F:36])([F:35])[F:34].O>CS(C)=O>[CH3:3][NH:4][C:5]1=[N:6][C:7](=[O:17])[S:8]/[C:9]/1=[CH:10]\[CH:11]1[CH2:16][CH2:15][N:14]([C:25]2[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][C:26]=2[C:33]([F:34])([F:36])[F:35])[CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 1442554-Fluoro-3-(trifluoromethyl)benzonitrileHCID 178482469HCID 178482469, compound

Product 1

HCID 178482468HCID 178482468, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of (5Z)-4-(methylamino)-5-(piperidin-4-ylmethylidene)-1,3-thiazol-2(5H)-one dihydrochloride (100 mg) in dimethyl sulfoxide (2 mL) were added cesium carbonate (327 mg) and 4-fluoro-3-(trifluoromethyl)benzonitrile (76 mg), and the mixture was stirred at 100° C. for 3 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/methanol) to give the title compound (14.5 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/methanol)

Sources & evidence

ORD record
ord-13665c12d87c4a29a3a2cf50e298fb12
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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