Hydrazine hydrate (1:1) → 6-cyclopropyl-N-(6-(hydrazinecarbonyl)pyridin-2-yl)-3,4'-bipyridine-2'-carboxamide

HRID 2178605

Reaktionsgleichung

Reaktionsgleichung von HRID 2178605
[CH:1]1([C:4]2[N:9]=[CH:8][C:7]([C:10]3[CH:15]=[CH:14][N:13]=[C:12]([C:16]([NH:18][C:19]4[N:24]=[C:23]([C:25]([O:27]C)=O)[CH:22]=[CH:21][CH:20]=4)=[O:17])[CH:11]=3)=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.O.[NH2:30][NH2:31]>C(O)C>[CH:1]1([C:4]2[N:9]=[CH:8][C:7]([C:10]3[CH:15]=[CH:14][N:13]=[C:12]([C:16]([NH:18][C:19]4[CH:20]=[CH:21][CH:22]=[C:23]([C:25]([NH:30][NH2:31])=[O:27])[N:24]=4)=[O:17])[CH:11]=3)=[CH:6][CH:5]=2)[CH2:3][CH2:2]1

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 66848750HCID 66848750, Verbindung

Produkt 1

HCID 581030166-cyclopropyl-N-(6-(hydrazinecarbonyl)pyridin-2-yl)-3,4'-bipyridine-2'-carboxamideAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

The methyl 6-(6-cyclopropyl-3,4′-bipyridine-2′-carboxamido)picolinate from the previous step were suspended in ethanol (20 mL), hydrazine hydrate (700 μL, 14.4 mmol) was added, and the reaction was heated to reflux for 4 hours. The reaction mixture was concentrated and the resultant solids were suspended in acetronitrile and collected by filtration. The solids were washed with acetonitrile (2×100 mL) and diethyl ether (2×100 mL), and dried under reduced pressure to afford 1.21 g (47% yield) of 6-cyclopropyl-N-(6-(hydrazinecarbonyl)pyridin-2-yl)-3,4′-bipyridine-2′-carboxamide as a white solid.

Aufarbeitung

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 4 hours
  3. concentrationThe reaction mixture was concentrated
  4. filtrationcollected by filtration
  5. washThe solids were washed with acetonitrile (2×100 mL) and diethyl ether (2×100 mL)
  6. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-06a479a41a2d46f1bbd978d2939b2a5f
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09067933B2

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