Dipropylamine → HCID 14390382, compound

HRID 2351752Notes

Reaction equation

HRID 2351752 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:18]([CH2:19][C:20]([OH:22])=O)[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(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:35]([NH:38][CH2:39][CH2:40][CH3:41])[CH2:36][CH3:37]>O1CCCC1>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:18]([CH2:19][C:20]([N:38]([CH2:39][CH2:40][CH3:41])[CH2:35][CH2:36][CH3:37])=[O:22])[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]

Participants

5

Reactant 3

HCID 8902DipropylamineHCID 682631,1'-CarbonyldiimidazoleHCID 14390459HCID 14390459, compound

Product 1

HCID 14390382HCID 14390382, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of crude 2-(4-nitrophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (3.0 g, 0.0101 mole), 1,1'-carbonyldi imidazole (1.63 g, 0.0101 mole) and dry tetrahydrofuran (100 ml) was stirred at room temperature for three hours with nitrogen bubbling through it and then refluxed under nitrogen overnight. The mixture was cooled to room temperature and a solution of dipropylamine (3.06 g, 0.0302 mole) in tetrahydrofuran (5 ml) was added. The suspension was refluxed over the weekend under nitrogen. The solvents were removed under reduced pressure and the solid residue was triturated in water (100 ml) overnight. The solid was collected by filtration, rinsed twice with water, twice with 5% potassium hydroxide solution and then twice more with water. The solid was dissolved in hot isopropyl alcohol, filtered while hot, and cooled to room temperature to precipitate a solid. Water was added and the solid was collected by filtration, rinsed with water and dried under high vacuum at 70° C. to give 1.23 g (32%) of title compound, mp. 205°-208° C.

Workup

  1. temperaturerefluxed under nitrogen overnight
  2. temperatureThe mixture was cooled to room temperature
  3. temperatureThe suspension was refluxed over the weekend under nitrogen
  4. customThe solvents were removed under reduced pressure
  5. customthe solid residue was triturated in water (100 ml) overnight
  6. filtrationThe solid was collected by filtration
  7. washrinsed twice with water, twice with 5% potassium hydroxide solution
  8. dissolutionThe solid was dissolved in hot isopropyl alcohol
  9. filtrationfiltered while hot, and
  10. temperaturecooled to room temperature
  11. customto precipitate a solid
  12. additionWater was added
  13. filtrationthe solid was collected by filtration
  14. washrinsed with water
  15. customdried under high vacuum at 70° C.

Sources & evidence

ORD record
ord-afd04f567b264ad3bc54936105c1f98a
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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