Hydrazine hydrate (1:1) → 6-[({[(1,2-dimethyl-1H-imidazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-amine

HRID 875218Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 875218
[CH3:1][N:2]1[C:6]([C:7](=[N:14][O:15][CH2:16][C:17]2[N:22]=[C:21]([N:23]3C(=O)C4C(=CC=CC=4)C3=O)[CH:20]=[CH:19][CH:18]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:5][N:4]=[C:3]1[CH3:34].O.NN>O1CCCC1>[CH3:1][N:2]1[C:6]([C:7](=[N:14][O:15][CH2:16][C:17]2[N:22]=[C:21]([NH2:23])[CH:20]=[CH:19][CH:18]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:5][N:4]=[C:3]1[CH3:34]

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 866507522-{6-[({[(1,2-dimethyl-1H-imidazol-5-yl)(phenyl)methylene]amino}-oxy)methyl]pyridin-2-yl}-1H-isoindole-1,3(2H)-dione

Produkt 1

HCID 866507536-[({[(1,2-dimethyl-1H-imidazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-amineAusbeute 50,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2-{6-[({[(1,2-dimethyl-1H-imidazol-5-yl)(phenyl)methylene]amino}-oxy)methyl]pyridin-2-yl}-1H-isoindole-1,3(2H)-dione (1.02 g, 2.26 mmol) in tetrahydrofuran (30 mL) was added dropwise hydrazine hydrate (0.55 mL, 11.3 mmol). After stirring at room temperature for 28 h, the reaction mixture was filtered, the insolubles washed with ethyl acetate, and the filtrate concentrated in vacuo. Purification on silica gel afforded 6-[({[(1,2-dimethyl-1H-imidazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-amine [370 mg, yield 43%; HPLC/MS: m/z=322 (M+H); log P(HCOOH)=0.39].

Aufarbeitung

  1. filtrationthe reaction mixture was filtered
  2. washthe insolubles washed with ethyl acetate
  3. concentrationthe filtrate concentrated in vacuo
  4. customPurification on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-7517e2328eaf43168d28e1607d083b5c
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08981111B2

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