Reaction equation
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]Participants
Procedure
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.
Workup
- temperaturerefluxed for 1 hour
- temperaturethe reaction was refluxed for 22 hours
- customThe reaction was quenched with water
- extractionextracted with Dichloromethane (three times)
- customthe combined organics were dried
- customevaporated
- customthe residue was purified on the
- customtriturated with diethyl ether
Sources & evidence
- ORD record
- ord-701a104241d34d2185bc7fe1ffdb9a31
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08501946B2
Linked notes
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