Sodium Bicarbonate → N-Cyclopropylmethyl-N-[7-iodo-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]amine

HRID 2253381Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2253381
[CH:1]1([CH2:4][N:5]([C:13]2[C:14]([S:23][CH3:24])=[N:15][N:16]3[C:21]([I:22])=[CH:20][CH:19]=[CH:18][C:17]=23)C(=O)OC(C)(C)C)[CH2:3][CH2:2]1.Cl.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[CH:1]1([CH2:4][NH:5][C:13]2[C:14]([S:23][CH3:24])=[N:15][N:16]3[C:21]([I:22])=[CH:20][CH:19]=[CH:18][C:17]=23)[CH2:2][CH2:3]1

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 21084196tert-butyl N-cyclopropylmethyl-N-[7-iodo-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]carbamateHCID 21866389Hydrogen chloride-ethyl acetate

Produkt 1

HCID 21084176N-Cyclopropylmethyl-N-[7-iodo-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of the crude tert-butyl N-cyclopropylmethyl-N-[7-iodo-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]carbamate dissolved in ethyl acetate (1 mL) was added 4N hydrochloric acid/ethyl acetate (10 mL), and the reaction mixture was stirred for 2 hours at room temperature. After completion of the reaction, saturated aqueous sodium bicarbonate was added to the reaction mixture while cooling with ice for neutralization. The reaction mixture was extracted with ethyl acetate, and after washing the organic extract with water and brine, it was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (20 g) and the title compound (506 mg) was obtained as a yellow oil from the ethyl acetate:n-hexane (1:3) fraction.

Aufarbeitung

  1. additionwas added to the reaction mixture
  2. temperaturewhile cooling with ice for neutralization
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. washafter washing the
  5. extractionorganic extract with water and brine, it
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (20 g)

Quellen und Nachweise

ORD-Eintrag
ord-54f10b977e064b1ab752794f4ce575cc
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07323569B2

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