Methanol → 7-{[2-Chloro-3-(trifluoromethyl)phenyl]carbonyl}-3-(methyloxy)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine

Reaktionsgleichung

Br[C:2]1[N:6]2[CH2:7][CH2:8][N:9]([C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[C:14]=3[Cl:23])=[O:12])[CH2:10][C:5]2=[N:4][N:3]=1.[Na].[CH3:25][OH:26]>>[Cl:23][C:14]1[C:15]([C:19]([F:22])([F:21])[F:20])=[CH:16][CH:17]=[CH:18][C:13]=1[C:11]([N:9]1[CH2:8][CH2:7][N:6]2[C:2]([O:26][CH3:25])=[N:3][N:4]=[C:5]2[CH2:10]1)=[O:12]

Komponenten

Edukt 3

HCID 887Methanol

HCID 5360545Sodium2×

HCID 665992213-Bromo-7-{[2-chloro-3-(trifluoromethyl)phenyl]carbonyl}-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine

Produkt 1

HCID 665990717-{[2-Chloro-3-(trifluoromethyl)phenyl]carbonyl}-3-(methyloxy)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine

Versuchsvorschrift

3-Bromo-7-{[2-chloro-3-(trifluoromethyl)phenyl]carbonyl}-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine (0.250 g, 0.610 mmol, see Example 1 for methods of preparation) was added to a solution of sodium (0.042 g, 1.831 mmol) in methanol (8 mL), under argon and refluxed for 1 hour. More sodium (0.040 g) was added and the reaction was refluxed for 22 hours. The reaction was quenched with water and extracted with Dichloromethane (three times), the combined organics were dried and evaporated, and the residue was purified on the mass-directed automated (preparative) HPLC (MDAP) and triturated with diethyl ether to give 7-{[2-chloro-3-(trifluoromethyl)phenyl]carbonyl}-3-(methyloxy)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine (0.082 g) as a white solid.