Triethylamine → N-(5-fluoro-2-methylphenyl)-tetrahydro-3,3-dimethyl-3H-oxazolo[3,4-a]pyrazine-7(8H)-acetamide
Reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[C:10]([F:12])[CH:9]=[CH:8][C:7]=1[CH3:13])=[O:4].[CH3:14][C:15]1([CH3:24])[N:19]2[CH2:20][CH2:21][NH:22][CH2:23][CH:18]2[CH2:17][O:16]1.C(N(CC)CC)C>CN(C)C=O>[F:12][C:10]1[CH:9]=[CH:8][C:7]([CH3:13])=[C:6]([NH:5][C:3](=[O:4])[CH2:2][N:22]2[CH2:21][CH2:20][N:19]3[C:15]([CH3:24])([CH3:14])[O:16][CH2:17][CH:18]3[CH2:23]2)[CH:11]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
A mixture of 6.6 parts of 2-chloro-N-(5-fluoro-2-methylphenyl)acetamide, 5 parts of hexahydro-3,3-dimethyl-3H-oxazolo[3,4-a]pyrazine, 6.1 parts of N,N-diethylethanamine and 67.5 parts of N,N-dimethylformamide was stirred and heated for 8 hours at about 70° C. After cooling overnight to room temperature, the reaction mixture was evaporated. The residue was dissolved in trichloromethane. The solution was washed with water, dried, filtered and evaporated, yielding 8.5 parts of N-(5-fluoro-2-methylphenyl)-tetrahydro-3,3-dimethyl-3H-oxazolo[3,4-a]pyrazine-7(8H)-acetamide as an oily residue (intermediate 121).
Workup
- temperatureAfter cooling overnight to room temperature
- customthe reaction mixture was evaporated
- dissolutionThe residue was dissolved in trichloromethane
- washThe solution was washed with water
- customdried
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-381c5c99556c4f848281c9ccb2896c0f
- Source dataset
- uspto-grants-1988_08
- Patent number
- US04766125
Reaction notes
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