Sodium Iodide → 1-(2-Isopropylpyrazolo[1,5-a]pyridin-3-yl)-2-(piperidin-1-yl)propan-1-one hydrochloride

HRID 731715Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 731715
[Cl:1][CH:2]([CH3:17])[C:3]([C:5]1[C:6]([CH:14]([CH3:16])[CH3:15])=[N:7][N:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=12)=[O:4].[NH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.[Na+].[I-]>CO>[ClH:1].[CH:14]([C:6]1[C:5]([C:3](=[O:4])[CH:2]([N:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[CH3:17])=[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][N:8]2[N:7]=1)([CH3:16])[CH3:15]

Komponenten

5

Edukt 3

HCID 5238Sodium IodideHCID 8082PiperidineHCID 215857512-Chloro-1-[2-(1-methylethyl)pyrazolo[1,5-a]pyridin-3-yl]-1-propanone

Produkt 1

HCID 685469031-(2-Isopropylpyrazolo[1,5-a]pyridin-3-yl)-2-(piperidin-1-yl)propan-1-one hydrochlorideAusbeute 26,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of 500 mg (2 mmol) of 2-chloro-1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)propan-1-one, 478 ul (4.8 mmol) of piperidine and 50 mg of NaI in 4 ml of MeOH was stirred at 50° C. overnight. The residue obtained after evaporation of the solvent was purified on an Al2O3 column. The fractions containing purified product were titrated with 4N HCl-dioxane to obtain a precipitate. Recrystallization from isopropanol/ether produced 175 mg of 1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)-2-(piperidin-1-yl)propan-1-one hydrochloride. Compound 1036.

Aufarbeitung

  1. customThe residue obtained
  2. customafter evaporation of the solvent
  3. customwas purified on an Al2O3 column
  4. additionThe fractions containing
  5. custompurified product
  6. customto obtain a precipitate
  7. customRecrystallization from isopropanol/ether

Quellen und Nachweise

ORD-Eintrag
ord-c0635d6c67444cab97a1d7d776cda9ca
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585875B2

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