Sodium Iodide → HCID 131730938, compound

HRID 2035487Notes

Reaction equation

HRID 2035487 reaction equation
[CH2:1]([NH:8][C:9]1[CH:14]=[C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:27][CH2:26][CH:25]([CH2:28][CH2:29]OS(C)(=O)=O)[CH2:24][CH2:23]3)=[CH:18][CH:17]=2)[N:12]=[CH:11][C:10]=1[CH2:35][C:36]([NH2:38])=[O:37])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-:39]#[N:40].[Na+].[I-].[Na+]>CN(C)C=O>[CH2:1]([NH:8][C:9]1[CH:14]=[C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:27][CH2:26][CH:25]([CH2:28][CH2:29][C:39]#[N:40])[CH2:24][CH2:23]3)=[CH:18][CH:17]=2)[N:12]=[CH:11][C:10]=1[CH2:35][C:36]([NH2:38])=[O:37])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 8929Sodium CyanideHCID 131730935HCID 131730935, compound2×

Product 1

HCID 131730938HCID 131730938, compoundYield 34.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

20 mg of 4-(benzylamino)-6-({4-[4-(2-methylsulfonyloxyethyl)piperidino]phenyl}amino)pyridine-3-carboxyamide (the compound of Example 58) was dissolved in 0.5 mL of N,N-dimethylformamide, to which 3 mg of sodium cyanide and 9 mg of sodium iodide were added, and stirred overnight at 120° C. After cooling, the solvent was evaporated, water was added to the residue, and extracted with chloroform. The extract was washed with water and dried on anhydrous sodium sulfate. The solvent was evaporated and the residue was purified by silica gel thin layer chromatography (chloroform:methanol=8:1) to obtain 6 mg (29%) of the title compound as a light yellow crystalline powder.

Workup

  1. additionwere added
  2. temperatureAfter cooling
  3. customthe solvent was evaporated
  4. additionwater was added to the residue
  5. extractionextracted with chloroform
  6. washThe extract was washed with water
  7. dry with materialdried on anhydrous sodium sulfate
  8. customThe solvent was evaporated
  9. customthe residue was purified by silica gel thin layer chromatography (chloroform:methanol=8:1)

Sources & evidence

ORD record
ord-15dea352ed524dc7b81d5b72e27c642c
Source dataset
uspto-grants-2013_11
Patent number
US08575153B2

Reaction notes

Loading…