Sodium Bicarbonate → N-Cyclopropyl-N-cyclopropylmethyl-N-[7-(2-methoxy-4,6-dimethylphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]amine

HRID 1865024

Reaktionsgleichung

Reaktionsgleichung von HRID 1865024
[CH:1]1([CH2:4][NH:5][C:6]2[C:7]([S:25][CH3:26])=[N:8][N:9]3[C:14]([C:15]4[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=4[O:23][CH3:24])=[CH:13][CH:12]=[CH:11][C:10]=23)[CH2:3][CH2:2]1.C([BH3-])#N.[Na+].C(=O)([O-])O.[Na+].C(O[C:39]1(O[Si](C)(C)C)[CH2:41][CH2:40]1)C>CO.C(O)(=O)C>[CH:39]1([N:5]([CH2:4][CH:1]2[CH2:2][CH2:3]2)[C:6]2[C:7]([S:25][CH3:26])=[N:8][N:9]3[C:14]([C:15]4[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=4[O:23][CH3:24])=[CH:13][CH:12]=[CH:11][C:10]=23)[CH2:41][CH2:40]1

Komponenten

7

Edukt 4

HCID 516892Sodium BicarbonateHCID 2734686(1-Ethoxycyclopropoxy)trimethylsilaneHCID 5003444Sodium cyanoborohydrideHCID 21984576N-cyclopropylmethyl-N-[7-(2-methoxy-4,6-dimethylphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]amine

Produkt 1

HCID 21984645N-Cyclopropyl-N-cyclopropylmethyl-N-[7-(2-methoxy-4,6-dimethylphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

After dissolving N-cyclopropylmethyl-N-[7-(2-methoxy-4,6-dimethylphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]amine (100 mg) in methanol (10 mL), ((1-ethoxycyclopropyl)oxy)trimethylsilane (60 μL), acetic acid (298 μL) and sodium cyanoborohydride (171 mg) were added and the mixture was heated to reflux for 6 hours. After cooling the reaction mixture to room temperature, saturated aqueous sodium hydrogencarbonate was added, extraction was performed with ethyl acetate, and the organic layer washed with brine. After drying the obtained organic layer over anhydrous magnesium sulfate and filtering it, the solvent was concentrated under reduced pressure, the residue was purified by silica gel column chromatography, and the title compound (74 mg) was obtained from the n-hexane:ethyl acetate (10:1) fraction as a yellow oil.

Aufarbeitung

  1. additionwere added
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 6 hours
  4. extractionextraction
  5. washthe organic layer washed with brine
  6. dry with materialAfter drying the obtained organic layer over anhydrous magnesium sulfate
  7. filtrationfiltering it
  8. concentrationthe solvent was concentrated under reduced pressure
  9. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-dfac9d693e7f4f6faa1e0812069e8755
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07625925B2

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