1,1'-Carbonyldiimidazole → HCID 14390421, compound

HRID 622023Notes

Reaction equation

HRID 622023 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]([C@H:17]([CH3:21])[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:22](N1C=CN=C1)([N:24]1C=CN=C1)=O>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:16]([C@H:17]([CH3:21])[C:18]([NH:24][CH3:22])=[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

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 14390428HCID 14390428, compound

Product 1

HCID 14390421HCID 14390421, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (R)-2-(4-chlorophenyl)-α-methyl-3H-imidazo[4,5-b]pyridine-3-acetic acid (5.0 g, 0.0166 mole), 1,1'carbonyldiimidazole (2.69 g, 0.0166 mole), and dry tetrahydrofuran (100 ml) was stirred at room temperature for 1.75 hours with a stream of nitrogen bubbling through it. A solution of methylene in tetrahydrofuran (33 ml of a 3.03M solution, 0.996 mole) was added and the reaction mixture was stirred at room temperature overnight under nitrogen. The solvents were removed under reduced pressure and the resulting solid was triturated in water, collected by filtration, rinsed twice with water, twice with 5% potassium hydroxide solution, and twice again with water. The solid was dissolved in hot isopropyl alcohol, charcoaled, and filtered while hot. Water was added to the cloud point, and upon cooling, solid precipitated. The solid was collected by filtration and dried under high vacuum at 50° C. overnight to give 3.21 g (62%) of title compound, mp 217°-218° C.

Workup

  1. customThe solvents were removed under reduced pressure
  2. customthe resulting solid was triturated in water
  3. filtrationcollected by filtration
  4. washrinsed twice with water, twice with 5% potassium hydroxide solution
  5. dissolutionThe solid was dissolved in hot isopropyl alcohol
  6. filtrationfiltered while hot
  7. additionWater was added to the cloud point
  8. temperatureupon cooling
  9. customsolid precipitated
  10. filtrationThe solid was collected by filtration
  11. customdried under high vacuum at 50° C. overnight

Sources & evidence

ORD record
ord-435cc73328ee41019812c357750fd70a
Source dataset
uspto-grants-1989_04
Patent number
US04824951

Reaction notes

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