Potassium Carbonate → N-(2-oxo-8-(2-oxopyrrolidin-1-yl)-1-(thiophen-3-ylmethyl)-1,2,3,4-tetrahydroquinolin-3-yl)acetamide

HRID 1887762Notes

Reaction equation

HRID 1887762 reaction equation
[O:1]=[C:2]1[CH:11]([NH:12][C:13](=[O:15])[CH3:14])[CH2:10][C:9]2[C:4](=[C:5]([N:16]3[CH2:20][CH2:19][CH2:18][C:17]3=[O:21])[CH:6]=[CH:7][CH:8]=2)[NH:3]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:29][C:30]1[CH:34]=[CH:33][S:32][CH:31]=1>C(C(C)=O)C>[O:1]=[C:2]1[CH:11]([NH:12][C:13](=[O:15])[CH3:14])[CH2:10][C:9]2[C:4](=[C:5]([N:16]3[CH2:20][CH2:19][CH2:18][C:17]3=[O:21])[CH:6]=[CH:7][CH:8]=2)[N:3]1[CH2:29][C:30]1[CH:34]=[CH:33][S:32][CH:31]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5207033-(Bromomethyl)thiopheneHCID 59620377N-(2-oxo-8-(2-oxopyrrolidin-1-yl)-1,2,3,4-tetrahydroquinolin-3-yl)acetamide

Product 1

HCID 59620372N-(2-oxo-8-(2-oxopyrrolidin-1-yl)-1-(thiophen-3-ylmethyl)-1,2,3,4-tetrahydroquinolin-3-yl)acetamide

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
79 °C

Procedure

Methyl ethyl ketone (5 mL) was added to a mixture of N-(2-oxo-8-(2-oxopyrrolidin-1-yl)-1,2,3,4-tetrahydroquinolin-3-yl)acetamide (500 mg) and potassium carbonate powder (265 mg), and 3-(bromomethyl)thiophene was added thereto. The mixture was stirred at an internal temperature of 79° C. for 20.5 hours, and then left to stand at room temperature. The mixture was partitioned between saturated aqueous sodium chloride solution (2 mL) and ethyl acetate (1 mL), and the aqueous layer was extracted with ethyl acetate (2 mL+1 mL). The organic layers were combined, and the solvent was evaporated under reduced pressure. Ethyl acetate (1.5 mL) and toluene (2.5 mL) were added to the thus-recovered residue, and the precipitated crystals were recovered through filtration. The container of the reaction mixture was washed with a mixture of ethyl acetate and toluene (3:5) (0.5 mL×2). The thus-recovered crystals were washed with a mixture of ethyl acetate and toluene (3:5) (1.0 mL×2), and then dried under reduced pressure at 60° C., whereby ethyl acetate solvates of the title compound (510 mg) were yielded.

Workup

  1. additionwas added
  2. waitleft
  3. customto stand at room temperature
  4. customThe mixture was partitioned between saturated aqueous sodium chloride solution (2 mL) and ethyl acetate (1 mL)
  5. extractionthe aqueous layer was extracted with ethyl acetate (2 mL+1 mL)
  6. customthe solvent was evaporated under reduced pressure
  7. additionEthyl acetate (1.5 mL) and toluene (2.5 mL) were added to the thus-recovered residue
  8. filtrationthe precipitated crystals were recovered through filtration
  9. washThe container of the reaction mixture was washed with a mixture of ethyl acetate and toluene (3:5) (0.5 mL×2)
  10. washThe thus-recovered crystals were washed with a mixture of ethyl acetate and toluene (3:5) (1.0 mL×2)
  11. customdried under reduced pressure at 60° C.
  12. customwere yielded

Sources & evidence

ORD record
ord-c1b12dc6e6844f4585d7389cc53bd4a2
Source dataset
uspto-grants-2013_08
Patent number
US08501772B2

Reaction notes

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