Potassium Cyanide → 2-[1-(4-cyanophenyl)-2,4-dioxo-1,3-diaza-spiro[4.5]dec-3-yl]-N-(2,6-diisopropylphenyl)acetamide

HRID 1966959Notes

Reaction equation

HRID 1966959 reaction equation
[C-:1]#[N:2].[K+].[CH:4]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH:13]([CH3:15])[CH3:14])[C:8]=1[NH:16][C:17](=[O:38])[CH2:18][N:19]1[C:23](=[O:24])[C:22]2([CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[N:21]([C:30]2[CH:35]=[CH:34][C:33](I)=[CH:32][CH:31]=2)[C:20]1=[O:37])([CH3:6])[CH3:5]>O1CCCC1.C(OCC)(=O)C.[Cu](I)I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([C:33]1[CH:34]=[CH:35][C:30]([N:21]2[C:22]3([CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[C:23](=[O:24])[N:19]([CH2:18][C:17]([NH:16][C:8]3[C:9]([CH:13]([CH3:15])[CH3:14])=[CH:10][CH:11]=[CH:12][C:7]=3[CH:4]([CH3:6])[CH3:5])=[O:38])[C:20]2=[O:37])=[CH:31][CH:32]=1)#[N:2]

Participants

7

Reactant 2

HCID 9032Potassium CyanideHCID 66681965N-(2,6-diisopropyl-phenyl)-2-[1-(4-iodo-phenyl)-2,4-dioxo-1,3-diaza-spiro[4.5]dec-3-yl]acetamide

Product 1

HCID 468924802-[1-(4-cyanophenyl)-2,4-dioxo-1,3-diaza-spiro[4.5]dec-3-yl]-N-(2,6-diisopropylphenyl)acetamide

Reagents, catalysts & solvents 4

HCID 83717Copper iodideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

38 mg (0.58 mmol, 2 eq.) of potassium cyanide and 5.5 mg (0.029 mmol, 0.1 eq.) of copper iodide are added to 170 mg (0.29 mmol, 1 eq.) of N-(2,6-diisopropyl-phenyl)-2-[1-(4-iodo-phenyl)-2,4-dioxo-1,3-diaza-spiro[4.5]dec-3-yl]acetamide in 10 ml of tetrahydrofuran. The reaction medium is degassed with nitrogen for 20 minutes, and 17 mg (0.015 μmol, 0.05 eq.) of tetrakis(triphenylphosphine)palladium are added. The medium is heated at 80° C. for 6 hours. The medium is cooled to room temperature and diluted with ethyl acetate, and then filtered through Celite. The filtrate is washed with water. The organic phases are combined. They are dried over sodium sulfate. The solvents are evaporated off and the residue is precipitated from dichloromethane and heptane. The product 2-[1-(4-cyanophenyl)-2,4-dioxo-1,3-diaza-spiro[4.5]dec-3-yl]-N-(2,6-diisopropylphenyl)acetamide is obtained in the form of a white solid.

Workup

  1. customThe reaction medium is degassed with nitrogen for 20 minutes
  2. temperatureThe medium is cooled to room temperature
  3. filtrationfiltered through Celite
  4. washThe filtrate is washed with water
  5. dry with materialThey are dried over sodium sulfate
  6. customThe solvents are evaporated off
  7. customthe residue is precipitated from dichloromethane and heptane

Sources & evidence

ORD record
ord-ba70a0632d2a4cd2a76f9d61e5b3b80a
Source dataset
uspto-grants-2013_04
Patent number
US08420682B2

Reaction notes

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