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

HRID 2351665
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2351665
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]([CH2:17][C:18]([OH:20])=[O:19])[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:4][CH:3]=1.[C:21]([N:28]1[CH:32]=[CH:31]N=[CH:29]1)(N1C=CN=C1)=O.[CH3:33][NH:34]N(CCC)NC>O1CCCC1>[OH2:19].[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:16]([CH2:17][C:18]([NH:34][CH2:33][CH2:31][CH2:32][N:28]([CH3:21])[CH3:29])=[O:20])[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:6][CH:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 682631,1'-CarbonyldiimidazoleHCID 143904574-chlorophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acidHCID 56982963N,N-dimethylaminopropylamine

Produkt 1

HCID 230373362-(4-Chlorophenyl)-N-[3-(dimethylamino)propyl]-3H-imidazo [4,5-b]pyridine-3-acetamide hydrochloride hydrate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

Under nitrogen bubbling, a mixture of 2-(4-chlorophenyl)-3H-imidazo [4,5-b]pyridine-3-acetic acid (5.0 g, 0.0174 mole) and 1,1'-carbonyldiimidazole (2.82 g, 0.0174 mole) in 150 ml of tetrahydrofuran was stirred at room temperature for 3 hrs. Under a nitrogen atmosphere, N,N-dimethylaminopropylamine (1.94 g, 0.019 mole) was added dropwise and the reaction was allowed to stir at room temperature overnight. The tetrahydrofuran was evaporated to dryness and the residue was treated with ice water. The solid was collected by filtration and dried under high vacuum. The solid was dissolved in isopropyl alcohol, acidified with ethereal hydrogen chloride, and seeded. The crystalline material was collected by filtration, washed with cold isopropyl alcohol, and dried under high vacuum at 50° C. over the weekend to give 2.78 g (34.5%), mp. 188°-90° C.

Aufarbeitung

  1. stirringto stir at room temperature overnight
  2. customThe tetrahydrofuran was evaporated to dryness
  3. additionthe residue was treated with ice water
  4. filtrationThe solid was collected by filtration
  5. customdried under high vacuum
  6. dissolutionThe solid was dissolved in isopropyl alcohol
  7. filtrationThe crystalline material was collected by filtration
  8. washwashed with cold isopropyl alcohol
  9. customdried under high vacuum at 50° C. over the weekend
  10. customto give 2.78 g (34.5%), mp. 188°-90° C.

Quellen und Nachweise

ORD-Eintrag
ord-b7dddde03a5d4917acf70278c208d779
Quelldatensatz
uspto-grants-1989_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04873251

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