Methylhydrazine → 3-ethyl-2-methoxy-6-methyl-5-(2-methyl-2H-[1,2,4]triazol-3-yl)-pyridine

HRID 1921359Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1921359
C[N:2]([CH:4]=[N:5][C:6](=O)[C:7]1[CH:12]=[C:11]([CH2:13][CH3:14])[C:10]([O:15][CH3:16])=[N:9][C:8]=1[CH3:17])C.[CH3:19][NH:20]N>C(O)(=O)C>[CH2:13]([C:11]1[C:10]([O:15][CH3:16])=[N:9][C:8]([CH3:17])=[C:7]([C:6]2[N:20]([CH3:19])[N:2]=[CH:4][N:5]=2)[CH:12]=1)[CH3:14]

Komponenten

4

Edukt 2

HCID 6061MethylhydrazineHCID 67492560N-dimethylaminomethylene-5-ethyl-6-methoxy-2-methylnicotinamide

Produkt 1

HCID 674922943-ethyl-2-methoxy-6-methyl-5-(2-methyl-2H-[1,2,4]triazol-3-yl)-pyridineAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

In a round bottom flask under a nitrogen atmosphere N-dimethylaminomethylene-5-ethyl-6-methoxy-2-methyl-nicotinamide (synthesized on 0.567 mmol scale) of Step 2, Example 16 is treated with glacial acetic acid (1 mL) followed by methylhydrazine (50 μL, 0.94 mmol). The resulting mixture is stirred at 90° C. for 12 hr. The reaction mixture is evaporated to dryness and the residue is purified by flash chromatography on a 5-gram silica gel cartridge by elution with dichloromethane:methanol (49:1). Fractions containing the product are combined, evaporated and re-purified by flash chromatography on a 5-gram silica gel cartridge by elution with dichloromethane:methanol (99:1). Fractions containing the product are combined and the solvent evaporated to give 3-ethyl-2-methoxy-6-methyl-5-(2-methyl-2H-[1,2,4]triazol-3-yl)-pyridine (80 mg, 61% yield) as a light yellow oil. MS: m/e=233 (M+H); 1H NMR (δ, ppm): 7.96 (1H, s), 7.29 (1H, s), 3.99 (3H, s), 3.74 (3H, s), 2.59 (2H, q), 2.30 (3H, s), 1.19 (3H, t).

Aufarbeitung

  1. customThe reaction mixture is evaporated to dryness
  2. customthe residue is purified by flash chromatography on a 5-gram silica gel cartridge by elution with dichloromethane:methanol (49:1)
  3. additionFractions containing the product
  4. customevaporated
  5. customre-purified by flash chromatography on a 5-gram silica gel cartridge by elution with dichloromethane:methanol (99:1)
  6. additionFractions containing the product
  7. customthe solvent evaporated

Quellen und Nachweise

ORD-Eintrag
ord-e0aff15e39114012b72b38ca06be45e8
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173682B2

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