Dimethylformamide → 2-(3-Fluoro-5-trifluoromethyl-phenyl)-N-methyl-N-(6-morpholin-4-yl-4-o-tolyl-pyridin-3-yl)-acetamide
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:12][C:13]([OH:15])=O)[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.C(N1[CH:27]=[CH:26]N=C1)(N1C=CN=C1)=O.C[NH:29][C:30]1[C:31]([C:36]2[CH:41]=[C:40]([N:42]3[CH2:47][CH2:46][O:45][CH2:44][CH2:43]3)[C:39]([CH3:48])=[CH:38][CH:37]=2)=[N:32][CH:33]=CC=1.[CH3:49]N(C)C=O>>[F:1][C:2]1[CH:3]=[C:4]([CH2:12][C:13]([N:32]([CH3:33])[C:31]2[CH:30]=[N:29][C:40]([N:42]3[CH2:43][CH2:44][O:45][CH2:46][CH2:47]3)=[CH:41][C:36]=2[C:37]2[CH:38]=[CH:39][CH:48]=[CH:49][C:26]=2[CH3:27])=[O:15])[CH:5]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:7]=1Participants
5
Reactant 4
Product 1
Procedure
To a solution of 266 mg (1.2 mmol) 3-fluoro-5-trifluoromethyl-phenylacetic acid in 7 ml N,N-dimethylformamide were added 195 mg (1.2 mmol) 1,1′-carbonyl-diimidazole and the solution was stirred for 30 min at room temperature. After addition of 283 mg (1 mmol) of methyl-(6-morpholin-4-yl-4-tolyl-pyridin-3-yl)-amine (as described in step f) for the preparation of Example 23), the reaction mixture was heated at 90° C. for 6 h. After cooling to room temperature, the solvent was removed in vacuo and the residue was re-dissolved in 30 ml ethyl acetate. The organic phase was washed with water (2×30 ml), brine, dried (magnesium sulfate) and evaporated. Flash chromatography gave 432 mg (88%) of the title compound as a light yellow foam.
Workup
- customfor the preparation of Example 23), the reaction mixture
- temperaturewas heated at 90° C. for 6 h
- temperatureAfter cooling to room temperature
- customthe solvent was removed in vacuo
- dissolutionthe residue was re-dissolved in 30 ml ethyl acetate
- washThe organic phase was washed with water (2×30 ml), brine
- dry with materialdried (magnesium sulfate)
- customevaporated
Sources & evidence
- ORD record
- ord-9a074564161844d6a284f34245f79d03
- Source dataset
- uspto-grants-2001_10
- Patent number
- US06297375B1
Reaction notes
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