N-(2-aminoethyl)acetamide → HCID 14390262, compound

HRID 1709472Notes

Reaction equation

HRID 1709472 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:19])[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[C:33]([NH:36][CH2:37][CH2:38][NH2:39])(=[O:35])[CH3:34]>O1CCCC1>[OH2:19].[C:33]([NH:36][CH2:37][CH2:38][NH:39][C:18](=[O:20])[CH2:17][N:16]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:10]2[N:9]=[C:8]1[C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)(=[O:35])[CH3:34]

Participants

5

Reactant 3

HCID 66082N-(2-aminoethyl)acetamideHCID 682631,1'-CarbonyldiimidazoleHCID 143904574-chlorophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 14390262HCID 14390262, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 2-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (5.0 g, 0.0174 mole), 1,1'-carbonyldiimidazole (2.82 g, 0.0174 mole) and dry tetrahydrofuran (100 ml) was stirred at room temperature for two hours with nitrogen bubbling through it. Solid N-acetylethylenediamine (4.44 g, 0.0435 mole) was added as well as 100 ml of tetrahydrofuran. A solid formed. After stirring overnight under nitrogen, the reaction mixture was evaporated to a white solid which was triturated in water (200 ml) overnight. The solid was collected by filtration, rinsed with water, dissolved in hot isopropyl alcohol and filtered hot. Water was added and the entire mixture was evaporated to a solid which was rinsed several times with light petroleum ether. The solid was dissolved in hot isopropyl alcohol and water was added to the cloud point. Upon cooling, solid precipitated, which was collected by filtration, and recrystallized again from isopropyl alcohol. Upon addition of water, the solid dissolved. All of the solvents were again evaporated under reduced pressure, and the resulting solid was again recrystallized from isopropyl alcohol to give 1.20 g (18%) of title compound, mp 247°-249° C.

Workup

  1. customA solid formed
  2. stirringAfter stirring overnight under nitrogen
  3. customthe reaction mixture was evaporated to a white solid which
  4. customwas triturated in water (200 ml) overnight
  5. filtrationThe solid was collected by filtration
  6. washrinsed with water
  7. dissolutiondissolved in hot isopropyl alcohol
  8. filtrationfiltered hot
  9. additionWater was added
  10. customthe entire mixture was evaporated to a solid which
  11. washwas rinsed several times with light petroleum ether
  12. dissolutionThe solid was dissolved in hot isopropyl alcohol
  13. additionwater was added to the cloud point
  14. temperatureUpon cooling
  15. customsolid precipitated
  16. filtrationwhich was collected by filtration
  17. customrecrystallized again from isopropyl alcohol
  18. additionUpon addition of water
  19. dissolutionthe solid dissolved
  20. customAll of the solvents were again evaporated under reduced pressure
  21. customthe resulting solid was again recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-fe37087a27534bab8870fbe905cc68ef
Source dataset
uspto-grants-1990_08
Patent number
US04948800

Reaction notes

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