Ethylenediamine → 2-Amino-6-methoxypyridine

HRID 31742

Reaktionsgleichung

Reaktionsgleichung von HRID 31742
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[N:3]=1.C(N)C[NH2:12]>>[CH3:9][O:8][C:4]1[N:3]=[C:2]([NH2:12])[CH:7]=[CH:6][CH:5]=1

Komponenten

3

Edukt 2

HCID 3301EthylenediamineHCID 870092-Chloro-6-methoxypyridine

Produkt 1

HCID 5800532-Amino-6-methoxypyridine

Versuchsvorschrift

2-Chloro-6-methoxypyridine (5.0 g) was heated with ethylenediamine (30 ml) at 120° C. overnight. The excess ethylenediamine was removed by rotary evaporation. The residue was dissolved in a small volume of 2.5 M aqueous sodium hydroxide and extracted thoroughly with dichloromethane. The combined organic layers were washed with saturated aqueous sodium chloride, dried over sodium sulfate and concentrated in vacuo to give (2-aminoethyl)(6-methoxy(2-pyridyl)amine as an orange syrup. The amine (2.58 g) was treated with benzotriazole carboxamidinium 4-methylbenzenesulfonate (0.86 g) and DIEA (0.45 mmol) in acetonitrile (6 ml) and stirred overnight at room temperature. Trituration with ether gave the guanidine, amino-{2-[(6-methoxy(2-pyridyl))amino]ethyl}carboxamidinium 4-methylbenzenesulfonate, as an oil. The oily guanidine (200 mg) was reacted with 100 mg of resin according to Resin Method C (90° C., overnight) to give the title compound.

Aufarbeitung

  1. customThe excess ethylenediamine was removed by rotary evaporation
  2. dissolutionThe residue was dissolved in a small volume of 2.5 M aqueous sodium hydroxide
  3. extractionextracted thoroughly with dichloromethane
  4. washThe combined organic layers were washed with saturated aqueous sodium chloride
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0a7c784ac2a9433a882046abc7284889
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425557B2

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