Hydrochloric Acid → Ethyl 4-(6-ethoxy-3-ethoxycarbonyl-7-methyl-1,8-naphthyridin-4-ylamino)phenoxyacetate hydrochloride

HRID 1956449Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1956449
[Cl:1][C:2]1[C:11]2[C:6](=[N:7][C:8]([CH3:15])=[C:9]([O:12][CH2:13][CH3:14])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17].Cl.[NH2:22][C:23]1[CH:33]=[CH:32][C:26]([O:27][CH2:28][C:29]([OH:31])=[O:30])=[CH:25][CH:24]=1.[N+]([C:37]1C=CC(OCC(O)=O)=C[CH:38]=1)([O-])=O.[H][H].Cl>[Pd]>[ClH:1].[CH2:13]([O:12][C:9]1[CH:10]=[C:11]2[C:6](=[N:7][C:8]=1[CH3:15])[N:5]=[CH:4][C:3]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:2]2[NH:22][C:23]1[CH:24]=[CH:25][C:26]([O:27][CH2:28][C:29]([O:31][CH2:37][CH3:38])=[O:30])=[CH:32][CH:33]=1)[CH3:14]

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 15720(4-Nitrophenoxy)acetic acidHCID 23198600Ethyl 4-chloro-6-ethoxy-7-methyl-1,8-naphthyridine-3-carboxylateHCID 668114882-(4-Aminophenoxy)acetic acid hydrochlorideHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 23209201Ethyl 4-(6-ethoxy-3-ethoxycarbonyl-7-methyl-1,8-naphthyridin-4-ylamino)phenoxyacetate hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23938PalladiumKatalysator

Versuchsvorschrift

A mixture of ethyl 4-chloro-6-ethoxy-7-methyl-1,8-naphthyridine-3-carboxylate (3.1 g), 4-aminophenoxy-acetic acid hydrochloride (2.17 g) (prepared by reduction of 4-nitrophenoxyacetic acid using hydrogen and 10% palladium charcoal in a similar manner to Example C1 followed by treatment with 5M hydrochloric acid and then evaporation) and absolute ethanol (30 ml) was boiled under reflux for 4 hours. The mixture was cooled to ambient temperature and filtered to give ethyl 4-(6-ethoxy-3-ethoxycarbonyl-7-methyl-1,8-naphthyridin-4-ylamino)phenoxyacetate hydrochloride, m.p. 192°-194° C. Active (1/1) at 30 mg/kg.

Aufarbeitung

  1. customevaporation) and absolute ethanol (30 ml)
  2. temperatureunder reflux for 4 hours
  3. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-37e46e3a8e6e4262905661911104d076
Quelldatensatz
uspto-grants-1998_07
Patentnummer
US05780482

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