Hydrochloric Acid → 2-Isopropyl-[1,2,4]triazolo[1,5-a]pyridin-7-amine

HRID 1802197Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1802197
[CH:1]([C:4]1[N:20]=[C:7]2[CH:8]=[C:9]([NH:12]C(=O)OC(C)(C)C)[CH:10]=[CH:11][N:6]2[N:5]=1)([CH3:3])[CH3:2].Cl>O1CCCC1>[CH:1]([C:4]1[N:20]=[C:7]2[CH:8]=[C:9]([NH2:12])[CH:10]=[CH:11][N:6]2[N:5]=1)([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 67774335Tert-butyl 2-isopropyl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamate

Produkt 1

HCID 677763492-Isopropyl-[1,2,4]triazolo[1,5-a]pyridin-7-amineAusbeute 62,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of tert-butyl 2-isopropyl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamate (400 mg, 1.45 mmol) in tetrahydrofurane (10 ml) is added hydrochloric acid (5 N in diethyl ether, 20 ml, 100 mmol). The resulting suspension is stirred for 18 hours at 25° C. The solvent is evaporated and the residue diluted with ethyl acetate, made basic with sodium hydroxide 2N and washed with water and brine. The organic layer is dried with magnesium sulfate and the solvent is evaporated under reduced pressure. The residue (416 mg) is purified by chromatography on a 20 g silicagel column using heptane/ethyl acetate 50-100% as eluent affording 2-isopropyl-[1,2,4]triazolo[1,5-a]pyridin-7-amine (159 mg, 62.3%) as a white solid. Mp.: 174-6° C. MS: m/z=177.2 (M+H+).

Aufarbeitung

  1. customThe solvent is evaporated
  2. additionthe residue diluted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialThe organic layer is dried with magnesium sulfate
  5. customthe solvent is evaporated under reduced pressure
  6. customThe residue (416 mg) is purified by chromatography on a 20 g silicagel column

Quellen und Nachweise

ORD-Eintrag
ord-7e5799e48443403bb646a05038fb75ac
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08349824B2

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