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

HRID 621944

Reaktionsgleichung

Reaktionsgleichung von HRID 621944
[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

Komponenten

6

Edukt 4

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

Produkt 1

HCID 143902882-(4-Chlorophenyl)-N-(cyclopropylmethyl)-3H-imidazo[4,5-b]pyridine-3-acetamideAusbeute 82,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Under nitrogen bubbling, a mixture of 2-(4-chlorophenyl)-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) were 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 ater, 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.

Aufarbeitung

  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 ater
  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

Quellen und Nachweise

ORD-Eintrag
ord-c7b3ea0a523542669750396f05f29954
Quelldatensatz
uspto-grants-1989_04
Patentnummer
US04824951

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