Reaction equation
[CH2:1]([NH:8][C:9](=[O:12])[CH2:10]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[F:22][C:23]1[CH:29]=[C:28]([F:30])[CH:27]=[C:26]([F:31])[C:24]=1[NH2:25]>CN(C=O)C.CCOC(C)=O>[CH2:1]([NH:8][C:9](=[O:12])[CH2:10][NH:25][C:24]1[C:23]([F:22])=[CH:29][C:28]([F:30])=[CH:27][C:26]=1[F:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
6
Conditions
- Temperature
- 100 °C
Procedure
A mixture of N-benzyl-2-chloroacetamide (700 mg—obtained as described for intermediate 1), DIPEA (0.76 mL) and 2,4,6-trifluoro-aniline (559 mg) in anhydrous DMF (5 mL) was stirred at 100° C. for 40 hours under a Nitrogen atmosphere. Then, more DIPEA (0.2 mL) was added and the mixture was heated to 100° C. for further 4 hours. After cooling to room temperature, the solution was diluted with AcOEt and washed with water and ice. The separated aqueous phase was extracted with further AcOEt (3×30 mL). The combined organic extracts were dried and concentrated in vacuo. The residue was purified by flash chromatography (CH/AcOEt from 8:2 to 6:4) to give the title compound (265 mg) as a beige solid.
Workup
- temperaturethe mixture was heated to 100° C. for further 4 hours
- temperatureAfter cooling to room temperature
- washwashed with water and ice
- extractionThe separated aqueous phase was extracted with further AcOEt (3×30 mL)
- customThe combined organic extracts were dried
- concentrationconcentrated in vacuo
- customThe residue was purified by flash chromatography (CH/AcOEt from 8:2 to 6:4)
Sources & evidence
- ORD record
- ord-626c79338a9e48f8986e663a161a5007
- Source dataset
- uspto-grants-2007_05
- Patent number
- US07214680B2
Linked notes
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