Sodium Carbonate → HCID 87402971, compound

HRID 1666647Notes

Reaction equation

HRID 1666647 reaction equation
[CH2:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6](O)[CH2:5][CH:4]=1)[CH3:2].[H-].[Na+].C1C=CC(N([S:30](C(F)(F)F)(=[O:32])=[O:31])S(C(F)(F)F)(=O)=O)=CC=1.C(=O)([O-])[O-:38].[Na+].[Na+].Cl.[NH2:44][C@H:45]1[CH2:49][CH2:48][N:47]([C:50](=[O:63])[CH2:51][C:52]2[CH:57]=[CH:56][C:55]([O:58][C:59]([F:62])([F:61])[F:60])=[CH:54][CH:53]=2)[CH2:46]1.C(=O)([O-])O.[Na+]>CN1CCCC1=O.C(OCC)(=O)C>[C:7]1([S:30]([OH:32])(=[O:38])=[O:31])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH2:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5]([NH:44][C@H:45]2[CH2:49][CH2:48][N:47]([C:50](=[O:63])[CH2:51][C:52]3[CH:53]=[CH:54][C:55]([O:58][C:59]([F:60])([F:61])[F:62])=[CH:56][CH:57]=3)[CH2:46]2)[CH:4]=1)[CH3:2]

Participants

9

Reactant 6

HCID 10340Sodium CarbonateHCID 24758Sodium hydrideHCID 142176Phenyl triflimideHCID 516892Sodium BicarbonateHCID 67442853HCID 67442853, compoundHCID 86636479(S)-1-(3-aminopyrrolidin-1-yl)-2-(4-trifluoromethoxyphenyl)ethanone mono hydrochloride

Product 1

HCID 87402971HCID 87402971, compoundYield 42.9%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

4-Ethylquinoline-1-ol (0.53 g) was dissolved in N-methylpyrrolidone (10 mL), followed by addition of sodium hydride (60% in oil, 130 mg), the mixture was stirred for 1 h, followed by addition of N-phenyl-trifluoromethane sulfonimide (1.33 g), and the mixture was stirred at room temperature for 1 h. To the reaction mixture were added sodium carbonate (0.39 g) and (S)-1-(3-aminopyrrolidin-1-yl)-2-(4-trifluoromethoxyphenyl)ethanone mono hydrochloride (1.1 g), and the mixture was stirred at 100° C. for 4 h. The reaction mixture was cooled to room temperature, followed by addition of ethyl acetate and saturated aqueous sodium hydrogencarbonate to separate the layers, and then the organic layer was washed with water and saturated brine and dried with anhydrous sodium sulfate. The desiccant was removed by filtration, the filtrate was concentrated under reduced pressure, then the residue was purified by silica gel column chromatography (NH silica gel, hexane/ethyl acetate=2:1). To the resulting residue in diethyl ether, benzenesulfonic acid monohydrate (163 mg) was added, and the precipitated crystals were collected by filtration to obtain the title compound (0.39 g).

Workup

  1. stirringthe mixture was stirred at room temperature for 1 h
  2. stirringthe mixture was stirred at 100° C. for 4 h
  3. customto separate the layers
  4. washthe organic layer was washed with water and saturated brine
  5. dry with materialdried with anhydrous sodium sulfate
  6. customThe desiccant was removed by filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (NH silica gel, hexane/ethyl acetate=2:1)
  9. additionTo the resulting residue in diethyl ether, benzenesulfonic acid monohydrate (163 mg) was added
  10. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-e1e365e4e4b14a9aba2856fb940520b7
Source dataset
uspto-grants-2011_10
Patent number
US08044068B2

Reaction notes

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