Ethylenediamine → HCID 131730933, compound

HRID 2035484Notes

Reaction equation

HRID 2035484 reaction equation
[CH2:1]([NH:8][C:9]1[CH:14]=[C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19](Br)=[CH:18][CH:17]=2)[N:12]=[CH:11][C:10]=1[CH2:23][C:24]([NH2:26])=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cu](C#N)[C:28]#[N:29].C(N)CN>CN1CCCC1=O>[CH2:1]([NH:8][C:9]1[CH:14]=[C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([C:28]#[N:29])=[CH:18][CH:17]=2)[N:12]=[CH:11][C:10]=1[CH2:23][C:24]([NH2:26])=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 131730934HCID 131730934, compoundHCID 178418260HCID 178418260, compound

Product 1

HCID 131730933HCID 131730933, compoundYield 14.9%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
180 °C

Procedure

20 mg of 4-(benzylamino)-6-[(4-bromophenyl)amino]pyridine-3-carboxyamide (the compound of Example 54) was dissolved in 0.4 mL of 1-methyl-2-pyrrolidinone, to which 5 mg of copper cyanide (I) was added, and stirred at 180° C. for 3 hours. After cooling, a 30% aqueous solution of ethylenediamine was added to the reaction mixture, 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=10:1) to obtain 2.3 mg (13%) of the title compound as a light brown solid.

Workup

  1. additionwas added
  2. temperatureAfter cooling
  3. extractionextracted with chloroform
  4. washthe extract was washed with water
  5. dry with materialdried on anhydrous sodium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was purified by silica gel thin layer chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-a073d59673ce49dabdf7d4e86ea5c36b
Source dataset
uspto-grants-2013_11
Patent number
US08575153B2

Reaction notes

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