Methyl 6-(cyclohexylamino)-5-nitronicotinate → Methyl 3-cyclohexyl-2-(4-hydroxyphenyl)-3H-imidazo[4,5-b]pyridine-6-carboxylate

HRID 392981Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 392981
[CH:1]1([NH:7][C:8]2[C:17]([N+:18]([O-])=O)=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][N:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[OH:22][C:23]1[CH:33]=[CH:32][C:26]([C:27](=N)OCC)=[CH:25][CH:24]=1>CO>[CH:1]1([N:7]2[C:8]3=[N:9][CH:10]=[C:11]([C:12]([O:14][CH3:15])=[O:13])[CH:16]=[C:17]3[N:18]=[C:27]2[C:26]2[CH:32]=[CH:33][C:23]([OH:22])=[CH:24][CH:25]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

4

Edukt 2

HCID 22660792Methyl 6-(cyclohexylamino)-5-nitronicotinateHCID 135442973Ethyl 4-hydroxybenzimidate hydrochloride

Produkt 1

HCID 135674093Methyl 3-cyclohexyl-2-(4-hydroxyphenyl)-3H-imidazo[4,5-b]pyridine-6-carboxylateAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of intermediate 58 (5.0 g, 20.0 mmol) and ethyl 4-hydroxybenzimidate hydrochloride (6.0 g, 30.0 mmol) in methanol (67 mL) was heated at reflux for 22 h. The reaction mixture was then cooled to rt and the precipitated solid was collected by vacuum filtration and washed sparingly with cold methanol to afford intermediate 59 as a white solid (6.13 g, 88%). ESI-MS m/e 352.2 (M+1).

Aufarbeitung

  1. temperatureat reflux for 22 h
  2. filtrationthe precipitated solid was collected by vacuum filtration
  3. washwashed sparingly with cold methanol

Quellen und Nachweise

ORD-Eintrag
ord-fb0db238a1b8436e86c5242a3d404d20
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06803374B2

Notizen zur Reaktion

Wird geladen…