Tetrahydrofuran → HCID 14390361, compound

HRID 2351733Notes

Reaction equation

HRID 2351733 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:21]([N:28]1[CH:32]=[CH:31][N:30]=[CH:29]1)(N1C=CN=C1)=O.O1CCC[CH2:34]1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:16]([CH2:17][C:18]([N:30]([CH2:31][CH2:32][N:28]([CH3:21])[CH3:34])[CH3:29])=[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 3

HCID 8028Tetrahydrofuran2×HCID 682631,1'-CarbonyldiimidazoleHCID 143904574-chlorophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 14390361HCID 14390361, compound

Procedure

A suspension of 2-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (5.0 g, 0.0174 mole), 1,1'-carbonyldiimidazole (2.82 g, 0.0174 mole) and dry tetrahydrofuran (100 ml) was stirred at room temperature for 2 hours with nitrogen bubbling through it, during which time a solution was formed. A solution of N,N,N'-trimethylenediamine (3.56 g, 0.0348 mole) in tetrahydrofuran (4.5 ml) was added and the solution was refluxed overnight under a nitrogen atmosphere. The solvents were removed under reduced pressure and the resulting oil was partitioned between water (100 ml) and ethyl acetate (100 ml). The layers were separated, the aqueous layer was re-extracted with ethyl acetate, and the combined organic layers were washed once with water, twice with 5% potassium hydroxide solution and twice with water. The organic layer was dried over sodium sulfate and evaporated under reduced pressure. The residue was recrystallized from isopropyl ether to give 3.5 g of product. A 1.0-g portion was dried at high vacuum overnight to give 0.63 g of title compound, mp 120°-122° C.

Workup

  1. customwas formed
  2. temperaturethe solution was refluxed overnight under a nitrogen atmosphere
  3. customThe solvents were removed under reduced pressure
  4. customthe resulting oil was partitioned between water (100 ml) and ethyl acetate (100 ml)
  5. customThe layers were separated
  6. extractionthe aqueous layer was re-extracted with ethyl acetate
  7. washthe combined organic layers were washed once with water, twice with 5% potassium hydroxide solution and twice with water
  8. dry with materialThe organic layer was dried over sodium sulfate
  9. customevaporated under reduced pressure
  10. customThe residue was recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-ae38a2b8b0a441c9b5577678b85ac17c
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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