1,1'-Carbonyldiimidazole → 3-[2-(4-Acetyl-1-piperazinyl)-2-oxoethyl]-2-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridine

HRID 2073078Notes

Reaction equation

HRID 2073078 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.[C:33]([N:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1)(=[O:35])[CH3:34]>O1CCCC1>[C:33]([N:36]1[CH2:41][CH2:40][N:39]([C:18](=[O:20])[CH2:17][N:16]2[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=[C:8]2[C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[CH2:38][CH2:37]1)(=[O:35])[CH3:34]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 837951-AcetylpiperazineHCID 143904574-chlorophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 143903773-[2-(4-Acetyl-1-piperazinyl)-2-oxoethyl]-2-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridineYield 57.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 2-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (4.0 g, 0.014 mole), 1,1'-carbonyldiimidazole (2.26 g, 0.014 mole) and dry tetrahydrofuran (80 ml) was stirred at room temperature for 3 hr with a stream of nitrogen bubbling through it. A solution of 1-acetylpiperazine (4.49 g, 0.035 mole) in tetrahydrofuran (10 ml) was added and the resulting suspension was heated at 60° C. overnight. The solvent was evaporated under reduced pressure and the residue was triturated in water (100 ml), filtered, and the filter cake rinsed with water. The solid was dissolved in hot isopropyl alcohol, filtered hot, and allowed to cool to room temperature. The resulting solid was collected by filtration and dried under high vacuum at 50° C. to yield 3.18 g (57%) of title compound, mp 217°-219° C.

Workup

  1. temperaturethe resulting suspension was heated at 60° C. overnight
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was triturated in water (100 ml)
  4. filtrationfiltered
  5. washthe filter cake rinsed with water
  6. dissolutionThe solid was dissolved in hot isopropyl alcohol
  7. filtrationfiltered hot
  8. temperatureto cool to room temperature
  9. filtrationThe resulting solid was collected by filtration
  10. customdried under high vacuum at 50° C.

Sources & evidence

ORD record
ord-ff78fb49e6cb4a0fba27a66ad02b9dae
Source dataset
uspto-grants-1990_04
Patent number
US04914109

Reaction notes

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