Potassium Carbonate → HCID 25181717, compound

HRID 1697070Notes

Reaction equation

HRID 1697070 reaction equation
[CH3:1][O:2][C:3](=[O:39])[C:4]([N:6]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19](=[O:38])[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([S:28]([N:31]2[CH2:36][CH2:35][N:34]([CH3:37])[CH2:33][CH2:32]2)(=[O:30])=[O:29])=[CH:24][CH:23]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=O.C([O-])([O-])=O.[K+].[K+]>CO>[CH3:1][O:2][C:3]([C:4]1[N:6]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:13]2[C:14]([C:19](=[O:38])[C:20]=1[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([S:28]([N:31]3[CH2:36][CH2:35][N:34]([CH3:37])[CH2:33][CH2:32]3)(=[O:29])=[O:30])=[CH:24][CH:23]=1)=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:39]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 59846287HCID 59846287, compound

Product 1

HCID 25181717HCID 25181717, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of N-(2-{3-[4-(4-methylpiperazine-1-sulfonyl)-phenyl]-propionyl}-phenyl)-N-phenyl-oxalamic acid methyl ester (ca. 0.5 mmol) and K2CO3 (128 mg) in MeOH (30 mL) was heated at reflux for 1 h. The reaction mixture was then cooled and evaporated under reduced pressure. The residue was partitioned between water (25 mL) and EtOAc (25 mL), the organic layer separated, and the aqueous layer extracted with EtOAc (2×25 mL). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude residue was purified twice by flash chromatography (DCM/MeOH) and once by preparative TLC (DCM/MeOH, 95:5) to afford 3-[4-(4-methylpiperazine-1-sulfonyl)-benzyl]-4-oxo-1-phenyl-1,4-dihydroquinoline-2-carboxylic acid methyl ester as light brown solid. MS=532.0 [M+H]+. MP=210.0-212.0° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 h
  3. temperatureThe reaction mixture was then cooled
  4. customevaporated under reduced pressure
  5. customThe residue was partitioned between water (25 mL) and EtOAc (25 mL)
  6. customthe organic layer separated
  7. extractionthe aqueous layer extracted with EtOAc (2×25 mL)
  8. washThe combined organic extracts were washed with brine
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customThe crude residue was purified twice by flash chromatography (DCM/MeOH) and once by preparative TLC (DCM/MeOH, 95:5)

Sources & evidence

ORD record
ord-218fb3dcb15e4e5295bcefa096aa3348
Source dataset
uspto-grants-2012_04
Patent number
US08163906B2

Reaction notes

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