Water → HCID 135923665, compound

HRID 455947Notes

Reaction equation

HRID 455947 reaction equation
[CH2:1]([CH:3]([CH:6]1[C:13]2[C:12]([C:14]3[CH:15]=[N:16][C:17]([O:20]C)=[CH:18][CH:19]=3)=[N:11][NH:10][C:9]=2[C:8](=[O:22])[N:7]1[C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:33]=[CH:32][O:31][N:30]=2)=[CH:25][CH:24]=1)[CH2:4][CH3:5])[CH3:2].[I-].[Na+].Cl[Si](C)(C)C.O>C(#N)C.C(OCC)(=O)C>[CH2:1]([CH:3]([CH:6]1[C:13]2[C:12]([C:14]3[CH:19]=[CH:18][C:17](=[O:20])[NH:16][CH:15]=3)=[N:11][NH:10][C:9]=2[C:8](=[O:22])[N:7]1[C:23]1[CH:24]=[CH:25][C:26]([C:29]2[CH:33]=[CH:32][O:31][N:30]=2)=[CH:27][CH:28]=1)[CH2:4][CH3:5])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 58045216HCID 58045216, compound

Product 1

HCID 135923665HCID 135923665, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4-(1-ethylpropyl)-5-(4-isoxazol-3-ylphenyl)-3-(6-methoxypyridin-3-yl)-4,5-dihydro-1H-pyrrolo[3,4-c]pyrazol-6-one (0.067 g, 0.15 mmol) and sodium iodide (0.067 g, 0.45 mmol) in acetonitrile (3 mL) was added chlorotrimethylsilane (0.058 mL, 0.45 mmol). The mixture was heated under reflux with stirring for 1 h. Water (50 mL) and ethyl acetate (50 mL) were added to the mixture, and the precipitate was collected by filtration and dried to give 4-(1-ethylpropyl)-5-(4-isoxazol-3-ylphenyl)-3-(6-oxo-1,6-dihydropyridin-3-yl)-4,5-dihydro-1H-pyrrolo[3,4-c]pyrazol-6-one (0.041 g, 64%) as slightly yellow crystals.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux
  3. filtrationthe precipitate was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-f8e82f4677e64150b56d3fd397cc7cf3
Source dataset
uspto-grants-2013_07
Patent number
US08497263B2

Reaction notes

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