Dipropylamine → HCID 14390335, compound

HRID 623055Notes

Reaction equation

HRID 623055 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[N:16]([CH2:17][C:18]([OH:20])=O)[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:33]([NH:36][CH2:37][CH2:38][CH3:39])[CH2:34][CH3:35]>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[N:16]([CH2:17][C:18]([N:36]([CH2:37][CH2:38][CH3:39])[CH2:33][CH2:34][CH3:35])=[O:20])[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8902DipropylamineHCID 682631,1'-CarbonyldiimidazoleHCID 14390205HCID 14390205, compound

Product 1

HCID 14390335HCID 14390335, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under nitrogen bubbling, a mixture of 2-(3-bromophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (4.98 g, 0.015 mole) and 1,1'-carbonyldiimidazole (2.59 g, 0.016 mole) in 120 ml of tetrahydrofuran was stirred at room temperature for 4 hrs. The di-n-propylamine (3.04 g, 0.03 mole) was added and the reaction mixture was heated at reflux for (65° C.) for 8-9 hrs. The reaction mixture was filtered and the filtrate was evaporated to an oil, which was placed under high vacuum for 3 hrs. The solid residue was treated with water, collected by filtration, washed with water, and dried under high vacuum. The solid was recrystallized from isopropyl alcohol-water, collected by filtration, washed with water, and dried under high vacuum to give 3.2 g (52%), mp 125°-27° C.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for (65° C.) for 8-9 hrs
  3. filtrationThe reaction mixture was filtered
  4. customthe filtrate was evaporated to an oil, which
  5. waitwas placed under high vacuum for 3 hrs
  6. additionThe solid residue was treated with water
  7. filtrationcollected by filtration
  8. washwashed with water
  9. customdried under high vacuum
  10. customThe solid was recrystallized from isopropyl alcohol-water
  11. filtrationcollected by filtration
  12. washwashed with water
  13. customdried under high vacuum
  14. customto give 3.2 g (52%), mp 125°-27° C.

Sources & evidence

ORD record
ord-2552ea302fa440dd97a7c90e475e16ea
Source dataset
uspto-grants-1988_09
Patent number
US04772600

Reaction notes

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