Dipropylamine → 2-(3,4-Dichlorophenyl)-N,N-dipropyl-3H-imidazo[4,5-b]pyridine-3-acetamide hydrate

HRID 623053Notes

Reaction equation

HRID 623053 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:17]([CH2:18][C:19](O)=[O:20])[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(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:34]([NH:37][CH2:38][CH2:39][CH3:40])[CH2:35][CH3:36]>O1CCCC1>[OH2:20].[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:17]([CH2:18][C:19]([N:37]([CH2:38][CH2:39][CH3:40])[CH2:34][CH2:35][CH3:36])=[O:20])[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

5

Reactant 3

HCID 8902DipropylamineHCID 682631,1'-CarbonyldiimidazoleHCID 156171932-(3,4-dichlorophenyl)3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 143903272-(3,4-Dichlorophenyl)-N,N-dipropyl-3H-imidazo[4,5-b]pyridine-3-acetamide hydrateYield 81.6%

Reagents, catalysts & solvents 1

HCID 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 120 ml of tetrahydrofuran was stirred at room temperature for 31/2 hrs. Then, under nitrogen atmosphere, dipropylamine (2.43 g, 0.024 mole) was added at room temperature and the reaction mixture was heated at reflux for 6 hrs. The reaction mixture was filtered, and the filtrate was evaporated to dryness. The residue was treated with water and refrigerated. The solid was collected by filtration, washed with water, and dried under high vacuum at 50°-60° C. overnight. The solid was recrystallized from isopropyl alcohol-water, collected, washed with water, and dried under high vacuum at 50°-60° C. overnight. Two crops gave 1.9 g (43%) of crystals, mp 122°-123° C.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 6 hrs
  3. filtrationThe reaction mixture was filtered
  4. customthe filtrate was evaporated to dryness
  5. additionThe residue was treated with water
  6. filtrationThe solid was collected by filtration
  7. washwashed with water
  8. customdried under high vacuum at 50°-60° C. overnight
  9. customThe solid was recrystallized from isopropyl alcohol-water
  10. customcollected
  11. washwashed with water
  12. customdried under high vacuum at 50°-60° C. overnight

Sources & evidence

ORD record
ord-6f9bb0125446474eaaf1b829764c1029
Source dataset
uspto-grants-1988_09
Patent number
US04772600

Reaction notes

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