Isobutyric Acid → Isobutyric acid N'-(5-fluoro-pyridin-2-yl)-hydrazide

HRID 1041910Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1041910
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH2:9])=[N:6][CH:7]=1.[C:10](O)(=[O:14])[CH:11]([CH3:13])[CH3:12].C1C=C2N=NN(O)C2=CC=1.O.CCN=C=NCCCN(C)C.Cl.Cl.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH:9][C:10](=[O:14])[CH:11]([CH3:13])[CH3:12])=[N:6][CH:7]=1

Komponenten

7

Edukt 5

HCID 6590Isobutyric AcidHCID 516892Sodium BicarbonateHCID 27960291-Hydroxybenzotriazole hydrateHCID 199167865-Fluoro-2-hydrazinylpyridineHCID 221413011-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride hydrochloride

Produkt 1

HCID 66977821Isobutyric acid N'-(5-fluoro-pyridin-2-yl)-hydrazideAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 5-fluoro-2-hydrazinyl-pyridine (0.59 g, 4.65 mmol), isobutyric acid (528 mg, 6 mmol), and HOBt hydrate (153 mg, 1 mmol) in DCM (10 mL) was treated with EDCl HCl (1.15 g, 6 mmol). The reaction mixture was stirred at RT for 40 min, poured onto sat. aq. sodium bicarbonate (40 mL), extracted with four portions of DCM, dried (Na2SO4), evaporated and purified by FCC (DCM/EtOAc 9/1 to 3/7) to give the title compound (0.42 g, 46%). LCMS (Method 8): Rt 2.46 min, m/z 198 [MH+].

Aufarbeitung

  1. extractionextracted with four portions of DCM
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. custompurified by FCC (DCM/EtOAc 9/1 to 3/7)

Quellen und Nachweise

ORD-Eintrag
ord-ea84c0ea6d1745678ce4a843ad17633e
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08557797B2

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