Dimethylamine → HCID 14390387, compound

HRID 622020Notes

Reaction equation

HRID 622020 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:18]([CH2:19][C:20](O)=[O:21])[C:13]3=[N:14][CH:15]=[CH:16][CH:17]=[C:12]3[N:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:23](N1C=CN=C1)([N:25]1C=CN=[CH:26]1)=O.CN(C)C=O.CNC>O1CCCC1>[CH3:23][N:25]([CH3:26])[C:20](=[O:21])[CH2:19][N:18]1[C:13]2=[N:14][CH:15]=[CH:16][CH:17]=[C:12]2[N:11]=[C:10]1[C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 6228DimethylformamideHCID 682631,1'-CarbonyldiimidazoleHCID 14390459HCID 14390459, compound

Product 1

HCID 14390387HCID 14390387, compoundYield 38.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 2-(4-nitrophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (3.0 g, 0.0101 mole), 1,1'-carbonyldiimidazole (1.6 g, 0.0101 mole), and dry dimethylformamide (10 ml) in tetrahydrofuran (100 ml) was stirred at room temperature for two hours with nitrogen bubbling through it. A solution of dimethylamine in tetrahydrofuran (26.4 ml of a 2.29M solution, 0.0606 mole) was added. The resulting solution was heated at 45° C. overnight under nitrogen. The solvents were evaporated under reduced pressure. The residue was triturated in water (300 ml), and the resulting solid was collected by filtration, rinsed with water, 5% potassium hydroxide solution and again with water. The solid was dissolved in hot isopropyl alcohol, filtered, and allowed to cool to room temperature. A solid precipitated which was collected by filtration and dried under high vacuum to give 1.26 g (38%) of title compound, mp 204°-207° C.

Workup

  1. temperatureThe resulting solution was heated at 45° C. overnight under nitrogen
  2. customThe solvents were evaporated under reduced pressure
  3. customThe residue was triturated in water (300 ml)
  4. filtrationthe resulting solid was collected by filtration
  5. washrinsed with water, 5% potassium hydroxide solution and again with water
  6. dissolutionThe solid was dissolved in hot isopropyl alcohol
  7. filtrationfiltered
  8. temperatureto cool to room temperature
  9. customA solid precipitated which
  10. filtrationwas collected by filtration
  11. customdried under high vacuum

Sources & evidence

ORD record
ord-e5ad19fc0f3b425bb753e796975cc676
Source dataset
uspto-grants-1989_04
Patent number
US04824951

Reaction notes

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