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

HRID 487615
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 487615
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-ethylpiperidineAusbeute 47,8 %

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), 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 to 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. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue was chromatographed on silica gel (40 g) with chloroform as an eluent
  9. additionThe fractions containing the object compound
  10. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-bf89d8a8629a4bcab8e9edc41d4d3c7c
Quelldatensatz
uspto-grants-1994_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05296490

Notizen zur Reaktion

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