Benzyloxyamine hydrochloride → 9,10-dihydro-8H-[1,2]oxazino[2',3':1,2]imidazo[4,5-c][1,5]naphthyridine

HRID 415519Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 415519
Cl[CH2:2][CH2:3][CH2:4][C:5]([NH:7][C:8]1[CH:9]=[N:10][C:11]2[C:16]([C:17]=1Cl)=[N:15][CH:14]=[CH:13][CH:12]=2)=O.Cl.C([O:27][NH2:28])C1C=CC=CC=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(O)(C)C>[N:15]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:16]=1[C:17]1[N:28]3[O:27][CH2:2][CH2:3][CH2:4][C:5]3=[N:7][C:8]=1[CH:9]=[N:10]2

Komponenten

5

Edukt 3

HCID 102312Benzyloxyamine hydrochlorideHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 66620109HCID 66620109, Verbindung

Produkt 1

HCID 666198299,10-dihydro-8H-[1,2]oxazino[2',3':1,2]imidazo[4,5-c][1,5]naphthyridineAusbeute 5,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A mixture of 4-chloro-N-(4-chloro[1,5]naphthyridin-3-yl)butanamide (3.1 g, 11 mmol) and O-benzylhydroxylamine hydrochloride (2.1 g, 13 mmol) in isopropanol (75 mL) was heated at reflux for 24 hours, then pyridinium p-toluenesulfonate (0.25 g, 1.0 mmol) was added and reflux continued for 48 more hours. The reaction mixture was then concentrated under reduced pressure and dichloromethane (50 mL) and saturated aqueous sodium carbonate (25 mL) were added and the mixture was stirred for 72 hours. The dichloromethane layer was then separated, concentrated under reduced pressure, and the residue purified by chromatography (silica gel eluted with 10% methanol in dichloromethane containing 5 mL of ammonium hydroxide solution per liter) to provide 0.13 g of 9,10-dihydro-8H-[1,2]oxazino[2′,3′:1,2]imidazo[4,5-c][1,5]naphthyridine.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 24 hours
  3. temperaturereflux
  4. concentrationThe reaction mixture was then concentrated under reduced pressure and dichloromethane (50 mL) and saturated aqueous sodium carbonate (25 mL)
  5. additionwere added
  6. customThe dichloromethane layer was then separated
  7. concentrationconcentrated under reduced pressure
  8. customthe residue purified by chromatography (silica gel eluted with 10% methanol in dichloromethane containing 5 mL of ammonium hydroxide solution per liter)

Quellen und Nachweise

ORD-Eintrag
ord-5b235e9df7744ec3991a5655baa4c94f
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088788B2

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