1,1'-Carbonyldiimidazole → HCID 14390451, compound

HRID 622054Notes

Reaction equation

HRID 622054 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:18][C:19](O)=[O:20])[C:9]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)=[N:10][C:5]2=[CH:4][CH:3]=1.[C:22](N1C=CN=C1)([N:24]1C=CN=C1)=O>O1CCCC1>[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:18][C:19]([NH:24][CH3:22])=[O:20])[C:9]([C:11]3[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=3)=[N:10][C:5]2=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 14390445HCID 14390445, compound

Product 1

HCID 14390451HCID 14390451, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-chloro-2-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (5.0 g, 0.0155 mole) and 1,1'-carbonyldiimidazol (2.52 g, 0.0155 mole) in dry tetrahydrofuran (100 ml) was refluxed under nitrogen for two hours. The solution was cooled to room temperature and a stream of nitrogen was bubbled through it for thirty minutes. A solution of methylamine in tetrahydrofuran (36 ml of a 2.59M solution, 0.0932 mole) was added and the suspension was stirred at room temperature under nitrogen for three days. The solvents were evaporated under reduced pressure and the resulting solid was triturated in water (100 ml), collected by filtration, and rinsed twice with water, twice with a 5% potassium hydroxide solution and twice again with water. The solid was dissolved in hot isopropyl alcohol, dried over magnesium sulfate, treated with charcoal and filtered while hot. The filtrate was reduced to one-half its original volume and isopropyl ether was added. Upon cooling to room temperature, solid precipitated, which was collected by filtration, rinsed with isopropyl ether and dried under high vacuum at 60° C. to give 3.45 g (66% yield) of title compound, mp >250° C.

Workup

  1. customa stream of nitrogen was bubbled through it for thirty minutes
  2. additionA solution of methylamine in tetrahydrofuran (36 ml of a 2.59M solution, 0.0932 mole) was added
  3. customThe solvents were evaporated under reduced pressure
  4. customthe resulting solid was triturated in water (100 ml)
  5. filtrationcollected by filtration
  6. washrinsed twice with water, twice with a 5% potassium hydroxide solution and twice again with water
  7. dissolutionThe solid was dissolved in hot isopropyl alcohol
  8. dry with materialdried over magnesium sulfate
  9. additiontreated with charcoal
  10. filtrationfiltered while hot
  11. additionwas added
  12. temperatureUpon cooling to room temperature
  13. customsolid precipitated
  14. filtrationwhich was collected by filtration
  15. washrinsed with isopropyl ether
  16. customdried under high vacuum at 60° C.

Sources & evidence

ORD record
ord-d2f85db782b549048b4c073af53bfd31
Source dataset
uspto-grants-1989_04
Patent number
US04824951

Reaction notes

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