Ethyl 5-aminopyridazine-4-carboxylate → 5-[2-(2,4,6-Trifluorophenyl)-acetylamino]-pyridazine-4-carboxylic acid ethyl ester

HRID 2217964

Reaktionsgleichung

Reaktionsgleichung von HRID 2217964
[CH2:1]([O:3][C:4]([C:6]1[C:11]([NH2:12])=[CH:10][N:9]=[N:8][CH:7]=1)=[O:5])[CH3:2].[F:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[C:16]([F:21])[C:15]=1[CH2:22][C:23](Cl)=[O:24]>C1(C)C=CC=CC=1.CN(C1C=CN=CC=1)C>[CH2:1]([O:3][C:4]([C:6]1[C:11]([NH:12][C:23](=[O:24])[CH2:22][C:15]2[C:16]([F:21])=[CH:17][C:18]([F:20])=[CH:19][C:14]=2[F:13])=[CH:10][N:9]=[N:8][CH:7]=1)=[O:5])[CH3:2]

Komponenten

5

Edukt 2

HCID 12352298Ethyl 5-aminopyridazine-4-carboxylateHCID 574280152,4,6-Trifluorophenylacetyl chloride

Produkt 1

HCID 689394245-[2-(2,4,6-Trifluorophenyl)-acetylamino]-pyridazine-4-carboxylic acid ethyl esterAusbeute 101,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

5-Aminopyridazine-4-carboxylic acid ethyl ester (1.26 g, prepared according to J. Het. Chem., (1968), 5, 845) was dissolved in dry toluene (125 ml) at 90° C., and DMAP (0.92 g) was added. 2,4,6-Trifluorophenylacetyl chloride (1.75 g of 95% purity material) was added dropwise with stirring at 70° C., and a white solid precipitated. The reaction was stirred at reflux for 5 hours and then filtered hot. The filtrate was evaporated to give 5-[2-(2,4,6-trifluorophenyl)-acetylamino]-pyridazine-4-carboxylic acid ethyl ester as a white solid (2.6 g), m.p. 143-144° C.

Aufarbeitung

  1. customa white solid precipitated
  2. stirringThe reaction was stirred
  3. temperatureat reflux for 5 hours
  4. filtrationfiltered hot
  5. customThe filtrate was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-00ec7cec4a364349b01b9e1274154ad2
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07410967B2

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