Hydrochloric Acid → 3-(3-{1-ethyl-5-[4-(trifluoromethyl)phenoxy]-1H-pyrazol-3-yl}phenyl)oxetan-3-amine
Reaction equation
Cl.O1CCOCC1.[CH2:8]([N:10]1[C:14]([O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)=[CH:13][C:12]([C:26]2[CH:27]=[C:28]([C:32]3([NH:36]S(C(C)(C)C)=O)[CH2:35][O:34][CH2:33]3)[CH:29]=[CH:30][CH:31]=2)=[N:11]1)[CH3:9]>CO>[CH2:8]([N:10]1[C:14]([O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:23])([F:24])[F:25])=[CH:18][CH:17]=2)=[CH:13][C:12]([C:26]2[CH:27]=[C:28]([C:32]3([NH2:36])[CH2:35][O:34][CH2:33]3)[CH:29]=[CH:30][CH:31]=2)=[N:11]1)[CH3:9]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of hydrochloric acid in dioxane (4 M, 1.55 mL, 6.2 mmol, 4.0 equiv) was added to a solution of N-[3-(3-{1-ethyl-5-[4-(trifluoromethyl)phenoxy]-1H-pyrazol-3-yl}phenyl)oxetan-3-yl]-2-methylpropane-2-sulfinamide (785 mg, 1.55 mmol, 1 equiv) in methanol (3.5 mL) at 22° C. The reaction mixture was stirred for 15 minutes, then was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The organic layer was washed with saturated aqueous sodium chloride solution, and the washed solution was dried over sodium sulfate. The dried solution was filtered, and the filtrate was concentrated to afford 3-(3-{1-ethyl-5-[4-(trifluoromethyl)phenoxy]-1H-pyrazol-3-yl}phenyl)oxetan-3-amine, which was used in the next step without further purification. Calc'd (M+1)+: 404.2. Found: 404.1.
Workup
- customwas partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
- washThe organic layer was washed with saturated aqueous sodium chloride solution
- dry with materialthe washed solution was dried over sodium sulfate
- filtrationThe dried solution was filtered
- concentrationthe filtrate was concentrated
Sources & evidence
- ORD record
- ord-648df87f48834425b4a173bd8fca58b3
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08871796B2
Reaction notes
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