Water → HCID 19756360, Verbindung

HRID 1587837Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1587837
[CH2:1]([O:3][C:4]([CH:6]([O:8][C:9]1[N:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[C:14]([CH2:19][CH3:20])[CH:13]=[C:12]2[O:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[C:35]2[N:36]=[N:37][N:38]([C:40]([C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[N:39]=2)=[CH:25][CH:24]=1)C)=[O:5])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[CH2:19]([C:14]1[CH:13]=[C:12]([O:21][CH2:22][C:23]2[CH:24]=[CH:25][C:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[C:35]3[N:36]=[N:37][N:38]([C:40]([C:53]4[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=4)([C:47]4[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=4)[C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)[N:39]=3)=[CH:27][CH:28]=2)[C:11]2[C:16](=[CH:17][CH:18]=[C:9]([O:8][CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[N:10]=2)[N:15]=1)[CH3:20]

Komponenten

6

Edukt 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 19756353HCID 19756353, VerbindungHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 19756360HCID 19756360, VerbindungAusbeute 90,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 6-[1-(ethoxycarbonyl)ethoxy]-2-ethyl-4-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methoxy]-1,5-naphthyridine (1.0 g) in THF (8 ml) was added to a stirred suspension of lithium aluminium hydride (100 mg) in THF (5 ml) at 0° C. The mixture was allowed to warm to ambient temperature and then stirred for 20 hours. Water (0.1 ml), 15% w/v sodium hydroxide solution (0.1 ml) and water (0.3 ml) were added and the mixture was stirred for 30 minutes. The insoluble solid was removed by filtration and the filtrate was concentrated by evaporation. The residue was triturated with ether to give 2-ethyl-6-(1-hydroxy-2-propoxy)-4-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methoxy]-1,5-naphthyridine (A) (0.89 g), m.p. 146°-150° C.; NMR (d6 -DMSO); 1.25-1.35(m, 6H), 2.8(q, 2H), 3.35-3.45(m, 1H), 3.6(s, 2H), 5.4(s, 2H), 6.8-6.9(m, 6H), 7.05-7.15(m, 3H), 7.2-7.4(m, 10H), 7.45-7.6(m, 5H), 7.8(dd, 1H), 8.1(d, 1H).

Aufarbeitung

  1. additionwere added
  2. stirringthe mixture was stirred for 30 minutes
  3. customThe insoluble solid was removed by filtration
  4. concentrationthe filtrate was concentrated by evaporation
  5. customThe residue was triturated with ether

Quellen und Nachweise

ORD-Eintrag
ord-a702a0267ff246fe8295aa8a5329a560
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05219863

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