StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Triethylamine → 1-[3-(2-Phenylpyrazolo[1,5-a]pyridin-3-yl)acryloyl]-2-ethylpiperidine

HRID 1029422
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1029422
ClC(OCC(C)C)=O.[C:9]1([C:15]2[C:23]([CH:24]=[CH:25][C:26](O)=[O:27])=[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][N:17]3[N:16]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(N(CC)CC)C.[CH2:36]([CH:38]1[CH2:43][CH2:42][CH2:41][CH2:40][NH:39]1)[CH3:37]>C(Cl)Cl.O1CCCC1>[C:9]1([C:15]2[C:23]([CH:24]=[CH:25][C:26]([N:39]3[CH2:40][CH2:41][CH2:42][CH2:43][CH:38]3[CH2:36][CH3:37])=[O:27])=[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][N:17]3[N:16]=2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 942052-EthylpiperidineHCID 53923255HCID 53923255, Verbindung

Produkt 1

HCID 540385431-[3-(2-Phenylpyrazolo[1,5-a]pyridin-3-yl)acryloyl]-2-ethylpiperidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344
Dichloromethane
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Isobutyl chloroformate (1.04 g) was added dropwise to a mixture of 3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)acrylic acid (trans isomer) (2.0 g) and triethylamine (0.766 g) in methylene chloride (40 ml) and tetrahydrofuran (10 ml) at -20° C. with stirring. After being stirred at the same temperature for 30 minutes, a solution of 2-ethylpiperidine (0.942 g) in tetrahydrofuran (10 ml) was added thereto dropwise at -20° C. and the mixture was stirred at -20° C. to 10° C. for 2 hours. The mixture was warmed to room temperature and evaporated in vacuo. A saturated sodium bicarbonate solution was added to the residue and extracted twice with chloroform (50 ml ). The combined extract was washed with saturated brine (50 ml), dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel (40 g) with chloroform as an eluent. The fractions containing the object compound were combined and evaporated in vacuo t give 1-[3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)acryloyl]-2-ethylpiperidine (trans isomer](1.30 g) as an oil.

Aufarbeitung

  1. stirringAfter being stirred at the same temperature for 30 minutes
  2. stirringdropwise at -20° C. and the mixture was stirred at -20° C. to 10° C. for 2 hours
  3. customevaporated in vacuo
  4. additionA saturated sodium bicarbonate solution was added to the residue
  5. extractionextracted twice with chloroform (50 ml )
  6. extractionThe combined extract
  7. washwas washed with saturated brine (50 ml)
  8. dry with materialdried over magnesium sulfate
  9. customevaporated in vacuo
  10. customThe residue was chromatographed on silica gel (40 g) with chloroform as an eluent
  11. additionThe fractions containing the object compound
  12. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3772d127d91d4ee19a37df5bdc4d51e9
Quelldatensatz
uspto-grants-1992_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05102869

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion