Sodium hydride → 6-chloro-N-isopropylthiazolo[4,5-c]pyridin-2-amine

HRID 1671799Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1671799
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][C:3]=1[NH2:9].[CH:10]([N:13]=[C:14]=[S:15])([CH3:12])[CH3:11].[H-].[Na+]>CN(C=O)C>[Cl:8][C:6]1[N:5]=[CH:4][C:3]2[N:9]=[C:14]([NH:13][CH:10]([CH3:12])[CH3:11])[S:15][C:2]=2[CH:7]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 75263Isopropyl IsothiocyanateHCID 5957294,6-Dichloropyridin-3-amine

Produkt 1

HCID 575272276-chloro-N-isopropylthiazolo[4,5-c]pyridin-2-amineAusbeute 61,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 4,6-dichloropyridin-3-amine (0.50 g, 3.07 mmol, 1.0 eq.) and isopropyl isothiocyanate (0.33 mL, 3.10 mmol, 1.0 eq.) in DMF under nitrogen at 0° C. was added NaH (60% in mineral oil, 0.194 g, 4.85 mmol, 1.6 eq.). After 10 min., the cold bath was removed, and the reaction mixture was stirred to room temperature for 10 min. It was then heated at 65° C. for 1 hr and cooled to room temperature. At 0° C., aqueous HCl (1 N), water and EtOAc were added, and the reaction mixture was stirred. The layers were separated, and the organic layer was washed with saturated aqueous NaHCO3 and brine, dried over Na2SO4, filtered and concentrated in vacuo. Silica gel chromatography using CH2Cl2:MeOH (100:1) as eluent afforded 6-chloro-N-isopropylthiazolo[4,5-c]pyridin-2-amine as a white solid (0.43 g, 61% yield).

Aufarbeitung

  1. customthe cold bath was removed
  2. temperatureIt was then heated at 65° C. for 1 hr
  3. temperaturecooled to room temperature
  4. additionAt 0° C., aqueous HCl (1 N), water and EtOAc were added
  5. stirringthe reaction mixture was stirred
  6. customThe layers were separated
  7. washthe organic layer was washed with saturated aqueous NaHCO3 and brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6880befbb1384728a5bb02008ff3b4ea
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07994337B2

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