Dipropylamine → HCID 14390330, compound

HRID 623050Notes

Reaction equation

HRID 623050 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:17]([CH2:18][C:19]([OH:21])=O)[C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[N:10]=2)=[CH:5][CH:4]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:34]([NH:37][CH2:38][CH2:39][CH3:40])[CH2:35][CH3:36]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:17]([CH2:18][C:19]([N:37]([CH2:38][CH2:39][CH3:40])[CH2:34][CH2:35][CH3:36])=[O:21])[C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[N:10]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 8902DipropylamineHCID 682631,1'-CarbonyldiimidazoleHCID 15617195HCID 15617195, compound

Product 1

HCID 14390330HCID 14390330, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under nitrogen bubbling, a mixture of 2-(4-methoxyphenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (4.2 g, 0.015 mole) and 1,1'-carbonyldiimidazole (2.43 g, 0.015 mole) in 120 ml of tetrahydrofuran was stirred at room temperature for 3 hrs. The dipropylamine (3.04 g, 0.03 mole) was added and the reaction mixture was allowed to stir at room temperature overnight, then heated at reflux for 8 hrs. The reaction mixture was filtered and the filtrate was evaporated to dryness, then placed under high vacuum over the weekend. The residue was treated with water and the solid was collected by filtration, washed wth water, and dried under high vacuum. The solid was dissolved in 100 ml of isopropyl alcohol, filtered, and the filtrate concentrated to 50 ml. The filtrate was diluted with water, seeded, and placed in a freezer overnight. The solid was collected by filtration, washed with water, and dried under high vacuum at 50°-60° C. overnight to give 1.8 g (33%) of title compound, mp 127°-29° C.

Workup

  1. stirringto stir at room temperature overnight
  2. temperatureheated
  3. temperatureat reflux for 8 hrs
  4. filtrationThe reaction mixture was filtered
  5. customthe filtrate was evaporated to dryness
  6. additionThe residue was treated with water
  7. filtrationthe solid was collected by filtration
  8. washwashed wth water
  9. customdried under high vacuum
  10. dissolutionThe solid was dissolved in 100 ml of isopropyl alcohol
  11. filtrationfiltered
  12. concentrationthe filtrate concentrated to 50 ml
  13. additionThe filtrate was diluted with water
  14. waitplaced in a freezer overnight
  15. filtrationThe solid was collected by filtration
  16. washwashed with water
  17. customdried under high vacuum at 50°-60° C. overnight

Sources & evidence

ORD record
ord-1e9a39b53e2c4e2badd0bf970603090d
Source dataset
uspto-grants-1988_09
Patent number
US04772600

Reaction notes

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