Water → HCID 135923665, compound

HRID 423188Notes

Reaction equation

HRID 423188 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-12f9c55a8a2b467a8b890d679e80a2b7
Source dataset
uspto-grants-2012_01
Patent number
US08101644B2

Reaction notes

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