Morpholine → HCID 69292803, compound
Reaction equation
C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:53][O:54][C:55]([C:57]1[S:58][C:59]([C:62](=[O:73])[NH:63][C@@H:64]([C:66]2[CH:71]=[CH:70][C:69](Br)=[CH:68][CH:67]=2)[CH3:65])=[CH:60][CH:61]=1)=[O:56].[NH:74]1[CH2:79][CH2:78][O:77][CH2:76][CH2:75]1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:53][O:54][C:55]([C:57]1[S:58][C:59]([C:62](=[O:73])[NH:63][C@@H:64]([C:66]2[CH:71]=[CH:70][C:69]([N:74]3[CH2:79][CH2:78][O:77][CH2:76][CH2:75]3)=[CH:68][CH:67]=2)[CH3:65])=[CH:60][CH:61]=1)=[O:56]Participants
Conditions
- Temperature
- 160 °C
Procedure
To a suspension of 1.0 mg (0.0045 mmol) palladium(II) acetate, 4.06 mg (0.0065 mmol) 2,2′-bis-(diphenylphosphino)-1,1′-binaphtyl (BINAP) and 125 mg (0.384 mmol) cesium carbonate in 1 ml dry toluene, 100 mg (0.272 mmol) (R)-5-[1-(4-Bromo-phenyl)-ethylcarbamoyl]-thiophene-2-carboxylic acid methyl ester (see example 1, step 1) and 30.0 mg (0.344 mmol) morpholine were added under an argon atmosphere. The mixture was heated in the microwave oven (Emrys Optimizer) at 160° C. for 15 min. After cooling to room temperature, the reaction mixture was filtered and the solid was washed with toluene. The solvent of the combined filtrates was evaporated and the crude product purified by preparative HPLC to yield 7.9 mg (0.021 mmol) (R)-5-[1-(4-Morpholin-4-yl-phenyl)-ethylcarbamoyl]-thiophene-2-carboxylic acid methyl ester.
Workup
- additionwere added under an argon atmosphere
- temperatureAfter cooling to room temperature
- filtrationthe reaction mixture was filtered
- washthe solid was washed with toluene
- customThe solvent of the combined filtrates was evaporated
- customthe crude product purified by preparative HPLC
Sources & evidence
- ORD record
- ord-23b3fe28301b4fec88659e7c6d9406b4
- Source dataset
- uspto-grants-2008_07
- Patent number
- US07396944B2
Reaction notes
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