Triethylamine → 2-(4-Chlorophenyl)-N-(cyclopropylmethyl)-3H-imidazo[4,5-b]pyridine-3-acetamide

HRID 2351684Notes

Reaction equation

HRID 2351684 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([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:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[NH2:34][CH2:35][CH:36]1[CH2:38][CH2:37]1.C(N(CC)CC)C>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:16]([CH2:17][C:18]([NH:34][CH2:35][CH:36]3[CH2:38][CH2:37]3)=[O:20])[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 81671(Cyclopropylmethyl)ammonium chlorideHCID 143904574-chlorophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 143902882-(4-Chlorophenyl)-N-(cyclopropylmethyl)-3H-imidazo[4,5-b]pyridine-3-acetamideYield 82.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under nitrogen bubbling, a mixture of 2-(4-chlorphenyl)-3H-imidazo [4,5-b]pyridine-3-acetic acid (4.0 g, 0.014 mole) and 1,1'-carbonyldiimidazole (2.27 g, 0.014 mole) in 150 ml of tetrahydrofuran was stirred at room temperature for 4 hours. Aminomethylcyclopropane hydrochloride (3.01 g, 0.028 mole) and triethylamine (2.83 g, 0.028 mole) was added and the reaction mixture was allowed to stir at room temperature overnight. The tetrahydrofuran was evaporated to dryness and the residue was treated with water. The solid was collected by filtration, washed with water, and dried under high vacuum overnight. The solid was recrystallized from isopropyl alcohol with cooling. The crystalline precipitate was collected by filtration, washed with cold isopropyl alcohol and water, and dried under high vacuum at 60° C. overnight to give 3.92 g (82%) of crystals, mp 228°-229° C.

Workup

  1. stirringto stir at room temperature overnight
  2. customThe tetrahydrofuran was evaporated to dryness
  3. additionthe residue was treated with water
  4. filtrationThe solid was collected by filtration
  5. washwashed with water
  6. customdried under high vacuum overnight
  7. customThe solid was recrystallized from isopropyl alcohol
  8. temperaturewith cooling
  9. filtrationThe crystalline precipitate was collected by filtration
  10. washwashed with cold isopropyl alcohol and water
  11. customdried under high vacuum at 60° C. overnight

Sources & evidence

ORD record
ord-8835ed8f7e70485a95504dcf4ea2de4c
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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