1,1'-Carbonyldiimidazole → 2-(3,4-Dichlorophenyl)-N-[2-(dimethylamino)ethyl]-3H-imidazo[4,5-b]pyridine-3-acetamide hydrochloride

HRID 623058Notes

Reaction equation

HRID 623058 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([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:6][C:7]=1[Cl:8].[C:22](N1C=CN=C1)([N:24]1[CH:28]=[CH:27][N:26]=[CH:25]1)=O.CNN(CC)NC>O1CCCC1.CC(C)=O>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:17]([CH2:18][C:19]([NH:26][CH2:27][CH2:28][N:24]([CH3:25])[CH3:22])=[O:21])[C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[N:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 156171932-(3,4-dichlorophenyl)3H-imidazo[4,5-b]pyridine-3-acetic acidHCID 57041336N,N-Dimethylaminoethylamine

Product 1

HCID 230373102-(3,4-Dichlorophenyl)-N-[2-(dimethylamino)ethyl]-3H-imidazo[4,5-b]pyridine-3-acetamide hydrochlorideYield 80.6%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under nitrogen bubbling, a mixture of 2-(3,4-dichlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (3.5 g, 0.011 mole) and 1,1'-carbonyldiimidazole (1.95 g, 0.011 mole) in 150 ml of tetrahydrofuran was stirred at room temperature for 2 hrs, then heated at 60°-65° C. for 2 hrs. N,N-Dimethylaminoethylamine (1.06 g, 0.012 mole) was added and the reaction mixture was allowed to stir at room temperature. The reaction mixture was filtered and the filtrate was evaporated to dryness, then placed under high vacuum overnight. The solid was treated with ice water, collected by filtration, washed with water, and dried under high vacuum at 50° overnight. The solid was dissolved in acetone and acidified with ethanolic hydrogen chloride. The crystalline precipitate was collected by filtration, washed with cold acetone, and dried under high vacuum to give 3.61 g. The solid was dissolved in 1.2 liters of acetone and concentrated to 600 ml to initiate crystallization. The solid was collected by filtration, washed with acetone, and dried under high vacuum overnight at 50° C. to give 1.9 g of title compound, mp 120°-122° C.

Workup

  1. temperatureheated at 60°-65° C. for 2 hrs
  2. stirringto stir at room temperature
  3. filtrationThe reaction mixture was filtered
  4. customthe filtrate was evaporated to dryness
  5. customplaced under high vacuum overnight
  6. additionThe solid was treated with ice water
  7. filtrationcollected by filtration
  8. washwashed with water
  9. customdried under high vacuum at 50° overnight
  10. dissolutionThe solid was dissolved in acetone
  11. filtrationThe crystalline precipitate was collected by filtration
  12. washwashed with cold acetone
  13. customdried under high vacuum
  14. customto give 3.61 g
  15. concentrationconcentrated to 600 ml
  16. customcrystallization
  17. filtrationThe solid was collected by filtration
  18. washwashed with acetone
  19. customdried under high vacuum overnight at 50° C.

Sources & evidence

ORD record
ord-ace8dae99f88452c9c3c79f1c6697132
Source dataset
uspto-grants-1988_09
Patent number
US04772600

Reaction notes

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