1,1'-Carbonyldiimidazole → HCID 14390447, compound

HRID 623133Notes

Reaction equation

HRID 623133 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:18][C:19]([OH:21])=[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(N1C=CN=C1)([N:24]1C=CN=C1)=O>O1CCCC1>[OH2:20].[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:18][C:19]([NH2:24])=[O:21])[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

Participants

4

Reactant 2

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

Product 1

HCID 14390447HCID 14390447, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 5-chloro-2-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (3.1 g, 0.00963 mole) and 1,1'-carbonyldiimidazole (1.56 g, 0.00963 mole) in tetrahydrofuran (100 ml) was refluxed under nitrogen for 1.5 hours, cooled to room temperature, and a stream of nitrogen was bubbled through the solution for one hour. The solution was cooled in a dry ice/acetone bath and liquid ammonium (50 ml) was added. The reaction mixture was allowed to warm to room temperature and was stirred at room temperature for two days. The solvents were removed under reduced pressure and the 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 recrystallized twice for isopropyl alcohol/water and dried under high vacuum at 70° C. to give 1.78 g (54%) of title cmpound, mp>250° C.

Workup

  1. temperaturewas refluxed under nitrogen for 1.5 hours
  2. customa stream of nitrogen was bubbled through the solution for one hour
  3. temperatureThe solution was cooled in a dry ice/acetone bath
  4. additionliquid ammonium (50 ml) was added
  5. temperatureto warm to room temperature
  6. customThe solvents were removed under reduced pressure
  7. customthe solid was triturated in water (100 ml)
  8. filtrationcollected by filtration
  9. washrinsed twice with water, twice with a 5% potassium hydroxide solution
  10. customThe solid was recrystallized twice for isopropyl alcohol/water
  11. customdried under high vacuum at 70° C.
  12. customto give 1.78 g (54%) of title cmpound, mp>250° C.

Sources & evidence

ORD record
ord-f1120062fa614a538cc46667a7d85393
Source dataset
uspto-grants-1988_09
Patent number
US04772600

Reaction notes

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