Triethylamine → 2-(4-Chlorophenyl)-N-[4-(dimethylamino)phenyl]-N-methyl-3H-imidazo [4,5-b]pyridine-3-acetamide

HRID 2073069Notes

Reaction equation

HRID 2073069 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]([CH2:17][C:18]([OH:20])=O)[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[CH3:27][N:28]([CH3:37])[C:29]1[CH:34]=[CH:33][C:32]([NH:35][CH3:36])=[CH:31][CH:30]=1.C(N(CC)CC)C>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:16]([CH2:17][C:18]([N:35]([C:32]3[CH:33]=[CH:34][C:29]([N:28]([CH3:27])[CH3:37])=[CH:30][CH:31]=3)[CH3:36])=[O:20])[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 5915951,4-Benzenediamine, N,N,N'-trimethyl-HCID 143904574-chlorophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 143903702-(4-Chlorophenyl)-N-[4-(dimethylamino)phenyl]-N-methyl-3H-imidazo [4,5-b]pyridine-3-acetamideYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 2-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (5.0 g, 0.0174 mole) in dry dimethylformamide (75 ml) was cooled in an ice bath and oxalyl chloride (2.2 g, 0.0172 mole) was added dropwise, with stirring, under nitrogen. The reaction mixture was stirred at room temperature for 3.5 hours and then N,N,N'-trimethyl-1,4-benzenediamine (2.9 g, 0.0193 mole) was added dropwise. The reaction mixture was stirred at room temperature under nitrogen overnight, poured into 400 ml of ice water and made basic with triethylamine (6 ml). The resulting white solid was collected by filtration, dissolved in hot isopropyl alcohol, treated with charcoal, and filtered while hot. Water was added to the cloud point and upon cooling, a solid precipitated. The gray solid was collected by filtration and rinsed with water to yield 6.6 g (92%) of product. A 1.0-g sample was dried under high vacuum to give 0.6 g of title compound, mp 152°-155° C.

Workup

  1. temperaturewas cooled in an ice bath
  2. stirringThe reaction mixture was stirred at room temperature for 3.5 hours
  3. stirringThe reaction mixture was stirred at room temperature under nitrogen overnight
  4. filtrationThe resulting white solid was collected by filtration
  5. dissolutiondissolved in hot isopropyl alcohol
  6. additiontreated with charcoal
  7. filtrationfiltered while hot
  8. additionWater was added to the cloud point
  9. temperatureupon cooling
  10. customa solid precipitated
  11. filtrationThe gray solid was collected by filtration
  12. washrinsed with water

Sources & evidence

ORD record
ord-3e04a6f683f64fb181b375430682c522
Source dataset
uspto-grants-1990_04
Patent number
US04914109

Reaction notes

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