Dipropylamine → HCID 14390436, compound

HRID 622007Notes

Reaction equation

HRID 622007 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:17][C:18]([OH:20])=[O:19])[C:10]3[C:11]([N:16]=2)=[N:12][CH:13]=[CH:14][CH:15]=3)=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:33]([NH:36][CH2:37][CH2:38][CH3:39])[CH2:34][CH3:35]>O1CCCC1>[OH2:19].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]([CH2:17][C:18]([N:36]([CH2:37][CH2:38][CH3:39])[CH2:33][CH2:34][CH3:35])=[O:20])[C:10]3[C:11]([N:16]=2)=[N:12][CH:13]=[CH:14][CH:15]=3)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8902DipropylamineHCID 682631,1'-CarbonyldiimidazoleHCID 14676659HCID 14676659, compound

Product 1

HCID 14390436HCID 14390436, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under nitrogen bubbling, a mixture of 2-(4-chlorophenyl)-1H-imidazo[4,5-b]pyridine-1-acetic acid (3.83 g, 0.013 mole) and 1,1'-carbonyldiimidazole (2.11 g, 0.013 mole) in 150 ml of tetrahydrofuran was stirred at room temperature for 4 hrs. Dipropylamine (2.63 g, 0.026 mole) was added and the reaction mixture was heated at reflux for 2 hrs, followed by standing at room temperature over the weekend. The tetrahydrofuran was evaporated to dryness and placed under high vacuum overnight. The residue was dissolved in isopropyl alcohol, filtered, and diluted with water to produce a crystalline product upon refrigeration. The solid was collected by filtration, washed with water, and dried under high vacuum overnight to give 1.22 g. A recrystallization from isopropyl alcohol-water gave 0.91 g of title compound after drying under high vacuum at 50° C. over the weekend, mp 139°-141° C.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 2 hrs
  3. customby standing at room temperature over the weekend
  4. customThe tetrahydrofuran was evaporated to dryness
  5. customplaced under high vacuum overnight
  6. dissolutionThe residue was dissolved in isopropyl alcohol
  7. filtrationfiltered
  8. additiondiluted with water
  9. customto produce a crystalline product upon refrigeration
  10. filtrationThe solid was collected by filtration
  11. washwashed with water
  12. customdried under high vacuum overnight
  13. customto give 1.22 g
  14. customA recrystallization from isopropyl alcohol-water

Sources & evidence

ORD record
ord-e6437acd104940e4be5ec742c0f071fe
Source dataset
uspto-grants-1989_04
Patent number
US04824951

Reaction notes

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