Diisopropylethylamine → 6-Methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-amine

HRID 1875885Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1875885
C(OC([NH:6][C:7]([NH2:9])=S)=O)C.[CH3:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([NH2:18])=[N:16][CH:17]=1.Cl.NO.CCN(C(C)C)C(C)C>C(O)C.CO>[CH3:10][O:11][C:12]1[CH:13]=[CH:14][C:15]2[N:16]([N:6]=[C:7]([NH2:9])[N:18]=2)[CH:17]=1

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochlorideHCID 866352895-Methoxypyridin-2-amine ethoxycarbonyl thiourea

Produkt 1

HCID 468640666-Methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-amineAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

To 5-methoxypyridin-2-amine ethoxycarbonyl thiourea (10.21 g, 40 mmol) in ethanol (57 mL) and methanol (57 mL) was added hydroxylamine hydrochloride (14 g, 200 mmol) and Hunig's Base (21 mL, 120 mmol). The mixture was stirred at room temperature for 2 hours, and then heated at 60° C. for 4 hours. The reaction was cooled to room temperature and filtered to remove solids. It was concentrated in vacuo and then suspended in chloroform. The solids were filtered off to yield 6-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-amine (6.05 g, 33.2 mmol, 83% yield). 1H NMR (300 MHz, DMSO-d6) δ ppm 8.30 (1H, d, J=1.83 Hz), 7.24-7.32 (1H, m), 7.16-7.23 (1H, m), 5.82 (2H, br. s.), 3.78 (3H, s). MS (LC/MS) R.T.=0.53; [M+H]+=165.2.

Aufarbeitung

  1. temperatureheated at 60° C. for 4 hours
  2. temperatureThe reaction was cooled to room temperature
  3. filtrationfiltered
  4. customto remove solids
  5. concentrationIt was concentrated in vacuo
  6. filtrationThe solids were filtered off

Quellen und Nachweise

ORD-Eintrag
ord-0cc47a3e61a04ebe973cb9c606d3a324
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08309577B2

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