Potassium Carbonate → HCID 59846208, compound

HRID 1697065Notes

Reaction equation

HRID 1697065 reaction equation
[CH3:1][O:2][C:3](=[O:40])[C:4]([N:6]([C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[C:20](=[O:39])[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([S:29]([N:32]2[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]2)(=[O:31])=[O:30])=[CH:25][CH:24]=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:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:13]2[C:14]([C:20](=[O:39])[C:21]=1[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([S:29]([N:32]3[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]3)(=[O:30])=[O:31])=[CH:25][CH:24]=1)=[CH:15][CH:16]=[C:17]([Cl:19])[CH:18]=2)=[O:40]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 59846237HCID 59846237, compound

Product 1

HCID 59846208HCID 59846208, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of N-(5-chloro-2-{3-[4-(4-methylpiperazine-1-sulfonyl)-phenyl]-propionyl}-phenyl)-N-phenyl-oxalamic acid methyl ester (1.1 mmol) and K2CO3 (282 mg) in MeOH (60 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 and EtOAc, the organic layer separated, and the aqueous layer extracted with EtOAc (2×25 mL). The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered, and evaporated under reduced pressure to give an orange-brown oil. The crude residue was purified twice by flash chromatography (DCM/MeOH) to give 7-chloro-3-[4-(4-methyl-piperazine-1-sulfonyl)-benzyl]-4-oxo-1-phenyl-1,4-dihydroquinoline-2-carboxylic acid methyl ester as light brown solid. MS=566 [M+H]+; MP=223.3-226.6° 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 and EtOAc
  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 anhydrous Na2SO4
  10. filtrationfiltered
  11. customevaporated under reduced pressure
  12. customto give an orange-brown oil
  13. customThe crude residue was purified twice by flash chromatography (DCM/MeOH)

Sources & evidence

ORD record
ord-0d92891bdab840fa86a40dd7b7b27a86
Source dataset
uspto-grants-2012_04
Patent number
US08163906B2

Reaction notes

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