HCID 22940234, compound → HCID 22940168, compound
Reaction equation
[OH:1]C1C=CC=CN=1.CC(C)([O-])C.[K+].ClC1N=N[C:18]([O:21][C:22]2[C:27]([CH3:28])=[C:26]([CH3:29])[CH:25]=[C:24]([CH3:30])[C:23]=2[CH:31](SCC)[CH3:32])=C(OC)C=1>CS(C)=O>[CH3:18][O:21][C:22]1[C:27]([CH3:28])=[C:26]([CH3:29])[CH:25]=[C:24]([CH3:30])[C:23]=1[C:31](=[O:1])[CH3:32]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
In dimethylsulfoxide (1 mL) was dissolved 34.0 mg (0.358 mmol) of 2-hydroxypyridine, 41.0 mg (0.366 mmol) of potassium tert-butoxide was added to the solution at room temperature, and the resulting mixture was stirred at room temperature for 20 minutes. To the mixture was added a dimethylsulfoxide (1 mL) solution containing 26.7 mg (0.0728 mmol) of 6-chloro-3-{2-[1-(ethylsulfanyl)ethyl]-3,5,6-trimethylphenoxy}-4-methoxypyridazine obtained in (1), and the resulting mixture was stirred at 60° C. After completion of the reaction, the reaction mixture was allowed to stand for cooling, and poured into water. After making the mixture acidic by adding hydrochloric acid to the mixture, and the mixture was extracted with ethyl acetate. The organic layers were combined, and washed successively with water and brine. After drying over anhydrous magnesium sulfate, the solvent was removed. The obtained residue was purified by preparative thin-layer chromatography (available from Merck Co., 1.05744, developed by ethyl acetate) to obtain 6.6 mg (0.019 mmol, Yield: 26%) of 6-chloro-3-{2-[1-(ethylsulfanyl)ethyl]-3,5,6-trimethylphenoxy}-4-pyridazinol (Compound No. 2606).
Workup
- additionwas added to the solution at room temperature
Sources & evidence
- ORD record
- ord-9c7fe8e367e64f9eaa302d0b43c3aa55
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07608563B2
Reaction notes
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