Reaktion #495737

Reaktionsgleichung

hydrochloric acid

3-methyl-1H-indazole-5-carbaldehyde

furan-2,4(3H,5H)-dione

3-amino-4,4,4-trifluorobut-2-enenitrile

→

title compound

4-(3-Methyl-1H-indazol-5-yl)-5-oxo-2-(trifluoromethyl)-1,4,5,7-tetrahydrofuro[3,4-b]pyridine-3-carbonitrile

Lösungsmittel

1-pentanol

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred at 100° C. for another 1 h
2. 2
   TemperaturAfter cooling
3. 3
   Sonstigethe mixture was directly purified by RP-HPLC (acetonitrile/water+0.1% TFA gradient)

Vorschrift

100 mg (0.624 mmol) 3-methyl-1H-indazole-5-carbaldehyde (Example 1A) and 62.5 mg (0.624 mmol) furan-2,4(3H,5H)-dione were heated up to reflux in 1-pentanol (3 ml) for 1 h. After addition of 425 mg (3.120 mmol) 3-amino-4,4,4-trifluorobut-2-enenitrile [A. W. Lutz, U.S. Pat. No. 3,635,977], the reaction mixture was stirred at 100° C. for further 4 h. Then, conc. hydrochloric acid (115 μl) and water (350 μl) were added, and the mixture was stirred at 100° C. for another 1 h. After cooling, the mixture was directly purified by RP-HPLC (acetonitrile/water+0.1% TFA gradient) to give 33 mg (14% of th.) of the title compound.

Quelle