Cesium fluoride → HCID 86598192, compound

HRID 895134Notes

Reaction equation

HRID 895134 reaction equation
[F-].[Cs+].[CH3:3][O:4][C:5](=[S:27])[NH:6][CH2:7][C:8]1[N:9]=[N:10][N:11]([C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]3)=[C:15]([F:26])[CH:14]=2)[CH:12]=1>C(O)C.C(OCC)(=O)C>[CH3:3][O:4][C:5](=[S:27])[NH:6][CH2:7][C:8]1[N:9]=[N:10][N:11]([C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][C:22](=[C:8]([C:12]#[N:11])[C:7]#[N:6])[CH2:21][CH2:20]3)=[C:15]([F:26])[CH:14]=2)[CH:12]=1

Participants

5

Reactant 2

HCID 25953Cesium fluorideHCID 20810181HCID 20810181, compound

Product 1

HCID 86598192HCID 86598192, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of malononitrilc (22 mg, 0.33 mmol) and CsF (42 mg, 0.28 mmol) in ethanol (5 ml) was added {1-[3-Fluoro-4-(4-oxo-piperidin-1-yl)-phenyl]-1H-[1,2,3]triazol-4-ylmethyl}-thiocarbamic acid O-methyl ester (100 mg, 0.28 mmol), obtained in Example 82. The reaction mixture was allowed to stir at room temperature for 2 h and then diluted with ethyl acetate (100 ml). The organic portion was washed with water followed by brine and dried over sodium sulfate. Removal of volatiles and purification of the resulting residue by silica gel column chromatography (ethyl acetate/pet. ether, 1:1), the title compound was obtained as white solid (45 mg, 40%). Mp. 198° C.

Workup

  1. customobtained in Example 82
  2. washThe organic portion was washed with water
  3. dry with materialdried over sodium sulfate
  4. customRemoval of volatiles and purification of the resulting residue by silica gel column chromatography (ethyl acetate/pet. ether, 1:1)

Sources & evidence

ORD record
ord-23a251b2a1ac4c968d79df222cb4c2a1
Source dataset
uspto-grants-2005_07
Patent number
US06914058B2

Reaction notes

Loading…