Dimethyl Sulfoxide → 4'-[3-(3-Oxo-1-pyrrolidinyl)propoxy][1,1'-biphenyl]-4-carbonitrile
Reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][C@@H:12]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][O:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[CH:31][C:30]([C:33]#[N:34])=[CH:29][CH:28]=3)=[CH:23][CH:22]=2)[CH2:13]1.C(N(CC)CC)C>C(Cl)Cl>[O:11]=[C:12]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][O:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:28]=[CH:29][C:30]([C:33]#[N:34])=[CH:31][CH:32]=3)=[CH:23][CH:22]=2)[CH2:13]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Oxalyl chloride (0.195 mmol) in dry CH2Cl2 (5 mL) under an atmosphere of nitrogen at −78° C. was treated with DMSO (0.39 mmol). After 15 minutes of stirring, the product from Example 153 was added and the mixture was stirred for another 15 minutes. Triethylamine (0.45 mmol) was added and the mixture was gradually allowed to warm to 0° C. The solution was partitioned between water (50 mL) and dichloromethane (50 mL). The organic layer was washed with brine (50 mL), dried over sodium sulfate and filtered. The filtrate was evaporated under reduced pressure and the residue purified by chromatography (CHCl3:MeOH:NH4OH, 9:1:0.1) to provide the title compound (60% yield).
Workup
- stirringthe mixture was stirred for another 15 minutes
- customThe solution was partitioned between water (50 mL) and dichloromethane (50 mL)
- washThe organic layer was washed with brine (50 mL)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- customThe filtrate was evaporated under reduced pressure
- customthe residue purified by chromatography (CHCl3:MeOH:NH4OH, 9:1:0.1)
Sources & evidence
- ORD record
- ord-e8ea387411d24c6b9bc3c922023d97be
- Source dataset
- uspto-grants-2003_02
- Patent number
- US06515013B2
Reaction notes
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