N,N-Diethylethylenediamine → HCID 14390350, compound

HRID 1709538Notes

Reaction equation

HRID 1709538 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(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:33]([N:35]([CH2:39][CH3:40])[CH2:36][CH2:37][NH2:38])[CH3:34]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:16]([CH2:17][C:18]([NH:38][CH2:37][CH2:36][N:35]([CH2:39][CH3:40])[CH2:33][CH3:34])=[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

5

Reactant 3

HCID 60993N,N-DiethylethylenediamineHCID 682631,1'-CarbonyldiimidazoleHCID 143904574-chlorophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 14390350HCID 14390350, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 2-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (6.0 g, 0.021 mole), 1,1'-carbonyldiimidazole (3.39 g, 0.021 mole) and dry tetrahydrofuran (100 ml) was stirred at room temperature for 3 hours with nitrogen bubbling through it. A solution of N,N-diethylethylenediamine (7.32 g, 0.063 mole) in tetrahydrofuran (10 ml) was added and the reaction mixture was stirred at room temperature under nitrogen overnight. The reaction mixture was evaporated to a solid. The solid was triturated with water (50 ml), filtered, and the filter cake was rinsed twice with water, twice with a 5% potassium hydroxide solution and twice with water. The resulting solid was dissolved in hot isopropyl alcohol, filtered hot and cooled to room temperature. Addition of water caused a white solid to form. The solid was collected by filtration and rinsed with water to give 4.21 g (52%) of a white solid. A 1.0-g sample of the solid was dried under high vacuum at room temperature to give a white solid, mp 142°-143° C.

Workup

  1. stirringthe reaction mixture was stirred at room temperature under nitrogen overnight
  2. customThe reaction mixture was evaporated to a solid
  3. customThe solid was triturated with water (50 ml)
  4. filtrationfiltered
  5. washthe filter cake was rinsed twice with water, twice with a 5% potassium hydroxide solution and twice with water
  6. dissolutionThe resulting solid was dissolved in hot isopropyl alcohol
  7. filtrationfiltered hot
  8. temperaturecooled to room temperature
  9. additionAddition of water
  10. customto form
  11. filtrationThe solid was collected by filtration
  12. washrinsed with water

Sources & evidence

ORD record
ord-0d942716f1374b9ca67e8219e53ffcc2
Source dataset
uspto-grants-1990_08
Patent number
US04948800

Reaction notes

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