Hydrazine hydrate (1:1) → (2-Ethyl-2H-indazol-5-yl)methanamine
Reaktionsgleichung
[CH2:1]([N:3]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH2:12][N:13]3C(=O)C4C(=CC=CC=4)C3=O)=[CH:9]2)=[N:4]1)[CH3:2].NN.O>CO>[CH2:1]([N:3]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH2:12][NH2:13])=[CH:9]2)=[N:4]1)[CH3:2]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 50 °C
Versuchsvorschrift
To a suspension of 2-((2-ethyl-2H-indazol-5-yl)methyl)isoindoline-1,3-dione (step-3 of Example 13, mixture) in MeOH (7 mL) was added hydrazine-H2O (0.5 mL), and the mixture was heated at 50° C. for 4 hrs. The mixture was concentrated, the residual white solid was added 2 M aqueous NaOH, and extracted with DCM, dried over Na2SO4, filtered and concentrated. The residual oil was diluted with MeOH and applied onto a strong cation exchange cartridge (BondElute (registered trademark) SCX, 1 g/6 mL, Varian Inc.), and the solid phase matrix was rinsed with MeOH (6 mL). The crude mixture was eluted with 1 M NH3 in MeOH (6 mL) and concentrated to give 68 mg (52% yield in 2 steps) of the titled compound as a colorless oil.
Aufarbeitung
- concentrationThe mixture was concentrated
- additionthe residual white solid was added 2 M aqueous NaOH
- extractionextracted with DCM
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- additionThe residual oil was diluted with MeOH
- washthe solid phase matrix was rinsed with MeOH (6 mL)
- washThe crude mixture was eluted with 1 M NH3 in MeOH (6 mL)
- concentrationconcentrated
Quellen und Nachweise
- ORD-Eintrag
- ord-788f0d62af2e41c9a3933edaf210dfee
- Quelldatensatz
- uspto-grants-2014_09
- Patentnummer
- US08829026B2
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