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

HRID 622013Notes

Reaction equation

HRID 622013 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-def6ba6d916640c3b02b387d47ec6aba
Source dataset
uspto-grants-1989_04
Patent number
US04824951

Reaction notes

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