Dimethylamine → HCID 14390385, compound

HRID 1709569Notes

Reaction equation

HRID 1709569 reaction equation
[Br:1][C:2]1[O:6][C:5]([C:7]2[N:15]([CH2:16][C:17]([OH:19])=O)[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[N:8]=2)=[CH:4][CH:3]=1.[C:20](N1C=CN=C1)([N:22]1C=CN=[CH:23]1)=O.CNC>O1CCCC1>[OH2:6].[Br:1][C:2]1[O:6][C:5]([C:7]2[N:15]([CH2:16][C:17]([N:22]([CH3:23])[CH3:20])=[O:19])[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 3

HCID 674DimethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 14390458HCID 14390458, compound

Product 1

HCID 14390385HCID 14390385, compoundYield 111%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 2-(5-bromo-2-furanyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (5.0 g, 0.0155 mole), and 1,1'-carbonyldiimidazole (2.52 g, 0.0155 mole) in dry tetrahydrofuran (100 ml) was stirred at room temperature for two hours with a stream of nitrogen bubbling through it. A solution of dimethylamine in tetrahydrofuran (40.6 ml of a 2.29M solution, 0.093 mole) was added, and the resulting solution was heated at 45° C. overnight under a nitrogen atmosphere. The reaction mixture was evaporated to a solid which 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, filtered, and allowed to cool to room temperature. Addition of water caused a precipitate to form which was collected by filtration, rinsed with water, and dried at high vacuum to give 3.16 g (58%) of title compound, mp 182°-185° C.

Workup

  1. temperaturethe resulting solution was heated at 45° C. overnight under a nitrogen atmosphere
  2. customThe reaction mixture was evaporated to a solid which
  3. customwas triturated in water (100 ml)
  4. filtrationcollected by filtration
  5. washrinsed twice with water, twice with a 5% potassium hydroxide solution
  6. dissolutionThe solid was dissolved in hot isopropyl alcohol
  7. filtrationfiltered
  8. temperatureto cool to room temperature
  9. additionAddition of water
  10. customto form which
  11. filtrationwas collected by filtration
  12. washrinsed with water
  13. customdried at high vacuum

Sources & evidence

ORD record
ord-e526488c063d4b24a7d7819dd3985e76
Source dataset
uspto-grants-1990_08
Patent number
US04948800

Reaction notes

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