Ethyl Beta-Carboline-3-Carboxylate → 3-(3-Cyclopropyl-1,2,4-oxadiazol-5-yl)-9H-beta-carboline

HRID 355817Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 355817
[O-]CC.[Na+].[Na].[CH:6]1([C:9](=[NH:11])[NH2:10])[CH2:8][CH2:7]1.C([O:14][C:15]([C:17]1[N:18]=[CH:19][C:20]2[NH:21][C:22]3[C:27]([C:28]=2[CH:29]=1)=[CH:26][CH:25]=[CH:24][CH:23]=3)=O)C>O.C(O)C.C1(C)C=CC=CC=1>[CH:6]1([C:9]2[N:10]=[C:15]([C:17]3[N:18]=[CH:19][C:20]4[NH:21][C:22]5[C:27]([C:28]=4[CH:29]=3)=[CH:26][CH:25]=[CH:24][CH:23]=5)[O:14][N:11]=2)[CH2:8][CH2:7]1

Komponenten

8

Edukt 4

HCID 105078Ethyl Beta-Carboline-3-CarboxylateHCID 431751CyclopropanecarboximidamideHCID 2723922Sodium ethoxideHCID 5360545Sodium

Produkt 1

HCID 189407253-(3-Cyclopropyl-1,2,4-oxadiazol-5-yl)-9H-beta-carbolineAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittel2×HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of sodium ethoxide, prepared from sodium metal (0.6 g, 26 mmol) and anhydrous ethanol (50 mL), cyclopropylmethanimidamide (1.67 g, 16 mmol) and 9H-β-carboline-3-carboxylic acid ethyl ester (2.0 g, 8.0 mmol) were added. Toluene (50 mL) was added and the resulting mixture was heated to 120°-130° C. The ethanol and water formed during the reaction were removed by azeotropic distillation. The reaction was complete after 30 min. The solid was filtered from the reaction mixture, washed with water and dried. This afforded the title compound (1.15 g, 52%) as an yellow solid. M.p. 256°-257° C.

Aufarbeitung

  1. additionwere added
  2. temperaturethe resulting mixture was heated to 120°-130° C
  3. customwere removed by azeotropic distillation
  4. filtrationThe solid was filtered from the reaction mixture
  5. washwashed with water
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-a5fa28fb02984bcaa1055039dc7cd15f
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05834482

Notizen zur Reaktion

Wird geladen…