Cyanuric chloride → HCID 21939849, compound

HRID 1242911Notes

Reaction equation

HRID 1242911 reaction equation
[N:1]1C(Cl)=NC(Cl)=NC=1Cl.[C:10]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:15]=[CH:14][C:13]([C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22](/[CH:25]=[CH:26]/[C:27](O)=O)=[CH:21][CH:20]=2)=[O:17])=[CH:12][CH:11]=1>CN(C)C=O>[C:27](/[CH:26]=[CH:25]/[C:22]1[CH:23]=[CH:24][C:19]([NH:18][C:16]([C:13]2[CH:14]=[CH:15][C:10]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:11][CH:12]=2)=[O:17])=[CH:20][CH:21]=1)#[N:1]

Participants

4

Reactant 2

HCID 7954Cyanuric chlorideHCID 21940042HCID 21940042, compound

Product 1

HCID 21939849HCID 21939849, compoundYield 65.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cyanuric chloride (727 mg, 3.94 mmol) was added to a dimethylformamide suspension of (E)-3-[4-[([1,1′-biphenyl]-4-ylcarbonyl)amino]phenyl]-2-propenic acid (900 mg, 2.63 mmol) obtained in Reference Example 74 at room temperature, which was stirred for 1 hour. After the solvent was distilled out under reduced pressure, the residue was dissolved in chloroform, which was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then the solvent was stilled out under reduced pressure. The resulting residue was purified by silica gel column chromatography (development solvent; chloroform:ethyl acetate=20:1), to give the titled compound (561 mg) as a colorless powder from diethyl ether.

Workup

  1. customobtained in Reference Example 74 at room temperature
  2. distillationAfter the solvent was distilled out under reduced pressure
  3. dissolutionthe residue was dissolved in chloroform
  4. washwhich was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe resulting residue was purified by silica gel column chromatography (development solvent; chloroform:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-52d640df42cd4f1e985ac99a49dc3f32
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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