Malononitrile → HCID 86598192, compound

HRID 1270351Notes

Reaction equation

HRID 1270351 reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].[F-].[Cs+].[CH3:8][O:9][C:10](=[S:32])[NH:11][CH2:12][C:13]1[N:14]=[N:15][N:16]([C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH2:29][CH2:28][C:27](=O)[CH2:26][CH2:25]3)=[C:20]([F:31])[CH:19]=2)[CH:17]=1>C(O)C.C(OCC)(=O)C>[CH3:8][O:9][C:10](=[S:32])[NH:11][CH2:12][C:13]1[N:14]=[N:15][N:16]([C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH2:29][CH2:28][C:27](=[C:2]([C:1]#[N:5])[C:3]#[N:4])[CH2:26][CH2:25]3)=[C:20]([F:31])[CH:19]=2)[CH:17]=1

Participants

6

Reactant 3

HCID 8010MalononitrileHCID 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 malononitrile (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-2f59d99137484b2eabfc47aba15e086c
Source dataset
uspto-grants-2007_04
Patent number
US07202254B2

Reaction notes

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