Hydrochloric Acid → [(7-{[(4-Fluorobenzyl)amino]carbonyl}-8-hydroxy[1,6]naphthyridin-5-yl)sulfanyl]acetic Acid

HRID 897305Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 897305
Br[C:2]1[N:11]=[C:10]([C:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[O:13])[C:9]([OH:23])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[SH:24][CH2:25][C:26]([OH:28])=[O:27].C(N(CC)CC)C.Cl>COCCOCCOC>[F:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][NH:14][C:12]([C:10]2[C:9]([OH:23])=[C:8]3[C:3]([CH:4]=[CH:5][CH:6]=[N:7]3)=[C:2]([S:24][CH2:25][C:26]([OH:28])=[O:27])[N:11]=2)=[O:13])=[CH:17][CH:18]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 1133Thioglycolic AcidHCID 8471TriethylamineHCID 223464015-bromo-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide

Produkt 1

HCID 22346250[(7-{[(4-Fluorobenzyl)amino]carbonyl}-8-hydroxy[1,6]naphthyridin-5-yl)sulfanyl]acetic Acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8150DiglymeLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A mixture of 5-bromo-N-(4-fluorobenzyl)-8-hydroxy-[1,6]naphthyridine-7-carboxamide (0.40 g, 1.05 mmol), mercaptoacetic acid (0.11 mL, 1.60 mmol), triethylamine (0.59 mL, 4.2 mmol) in diglyme (2.5 mL) was heated with stirring at 130° C. under an atmosphere of nitrogen for 18 hours. The product mixture was treated with 1 M aq HCl at 0° C. The resulting yellow solid was filtered, washed with diethyl ether to provide the title acid.

Aufarbeitung

  1. temperaturewas heated
  2. filtrationThe resulting yellow solid was filtered
  3. washwashed with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-97b8e5b46c914587aeadb78523057474
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06921759B2

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