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Ethyl orthopropionate → 1-(7-bromo-2-ethyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)-2-methylpropan-2-ol

HRID 598028
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 598028
[C:1](OCC)(OCC)(OCC)[CH2:2][CH3:3].[NH2:13][C:14]1[CH:15]=[N:16][C:17]2[C:22]([C:23]=1[NH:24][CH2:25][C:26]([CH3:29])([OH:28])[CH3:27])=[N:21][CH:20]=[C:19]([Br:30])[CH:18]=2>C1(C)C=CC=CC=1.Cl.N1C=CC=CC=1>[Br:30][C:19]1[CH:20]=[N:21][C:22]2[C:23]3[N:24]([CH2:25][C:26]([CH3:27])([OH:28])[CH3:29])[C:1]([CH2:2][CH3:3])=[N:13][C:14]=3[CH:15]=[N:16][C:17]=2[CH:18]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 66995Ethyl orthopropionateHCID 670523831-[(3-Amino-7-bromo[1,5]naphthyridin-4-yl)amino]-2-methylpropan-2-ol

Produkt 1

HCID 670524201-(7-bromo-2-ethyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)-2-methylpropan-2-olAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 10176127Pyridinium chlorideKatalysatorHCID 1140
Toluene
Lösungsmittel

Versuchsvorschrift

Pyridine hydrochloride (0.095 g, 0.82 mmol) and triethyl orthopropionate (6.36 g, 36.1 mmol) were sequentially added to a solution of 1-[(3-amino-7-bromo[1,5]naphthyridin-4-yl)amino]-2-methylpropan-2-ol (10.2 g, 32.8 mmol) in toluene (200 mL), and the resulting mixture was heated at reflux for three hours. Most of the solvent was removed under reduced pressure, and a solid was present. The solid was isolated by filtration and dried to provide 8.59 g of 1-(7-bromo-2-ethyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)-2-methylpropan-2-ol as a light yellow solid. A small portion of the solid was recrystallized from acetonitrile to provide an off-white solid, mp 207-208° C.

Aufarbeitung

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for three hours
  3. customMost of the solvent was removed under reduced pressure
  4. customThe solid was isolated by filtration
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-fc0d6256ac6c45888fb4663d028aceb8
Quelldatensatz
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07897609B2

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