Tetrahydrofuran → HCID 14390390, compound

HRID 1709573Notes

Reaction equation

HRID 1709573 reaction equation
[Br:1][C:2]1[O:6][C:5]([C:7]2(CC(O)=O)[NH:15][C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[NH:8]2)=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:32]([NH:35][CH2:36][CH2:37][CH3:38])[CH2:33][CH3:34].[O:39]1CC[CH2:41][CH2:40]1>>[Br:1][C:2]1[O:6][C:5]([C:7]2[N:15]([CH2:41][C:40]([N:35]([CH2:36][CH2:37][CH3:38])[CH2:32][CH2:33][CH3:34])=[O:39])[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[N:8]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 8902DipropylamineHCID 682631,1'-CarbonyldiimidazoleHCID 86742455HCID 86742455, compound

Product 1

HCID 14390390HCID 14390390, compoundYield 32%

Procedure

A suspension of 2-(5-bromo-2-furanyl)-3H-imidazo[4,5-b]pyridine acetic acid (5.0 g, 0.0155 mole), 1,1'-carbonyldiimidazole (2.52 g, 0.0155 mole) and dry tetrahydrofuran (100 ml) was stirred at room temperature for 2.5 hours with a stream of nitrogen bubbling through it. A solution of dipropylamine 4.71 g, 0.046 mole) in tetrahydrofuran (6 ml) was added and the reaction mixture was refluxed for 15 hours, then stirred at room temperature. The solvents were removed under reduced pressure, and the resulting oil was partitioned between ethyl acetate (100 ml) and water (100 ml). The layers were separated, and the aqueous layer was re-extracted with ethyl acetate. The combined organic layers were washed with water, twice with a 5% potassium hydroxide solution and twice again with water, dried with magnesium sulfate, charcoaled, and filtered. The solvent was removed under reduced pressure to give an oil which crystallized upon trituration with isopropyl ether. The solid was collected by filtration and dried under high vacuum to give 2.0 g (32%) of title compound, mp 102°-104° C.

Workup

  1. temperaturethe reaction mixture was refluxed for 15 hours
  2. stirringstirred at room temperature
  3. customThe solvents were removed under reduced pressure
  4. customthe resulting oil was partitioned between ethyl acetate (100 ml) and water (100 ml)
  5. customThe layers were separated
  6. extractionthe aqueous layer was re-extracted with ethyl acetate
  7. washThe combined organic layers were washed with water, twice with a 5% potassium hydroxide solution and twice again with water
  8. dry with materialdried with magnesium sulfate
  9. filtrationfiltered
  10. customThe solvent was removed under reduced pressure
  11. customto give an oil which
  12. customcrystallized upon trituration with isopropyl ether
  13. filtrationThe solid was collected by filtration
  14. customdried under high vacuum

Sources & evidence

ORD record
ord-6ee9163b6b954574b604ca5343c2531c
Source dataset
uspto-grants-1990_08
Patent number
US04948800

Reaction notes

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