Water → HCID 23019633, compound

HRID 1354194Notes

Reaction equation

HRID 1354194 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([C:32]([O:34]CC)=[O:33])[C:7](=[O:31])[N:8]3[C:13]=2[C:12]([CH3:14])=[C:11]([C:15]2[CH:20]=[CH:19][C:18]([NH:21][CH2:22][CH2:23][O:24]C4CCCCO4)=[CH:17][CH:16]=2)[CH:10]=[CH:9]3)[CH2:3][CH2:2]1.O.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C(=O)([O-])O.[Na+]>C(O)C>[CH:1]1([C:4]2[CH:5]=[C:6]([C:32]([OH:34])=[O:33])[C:7](=[O:31])[N:8]3[C:13]=2[C:12]([CH3:14])=[C:11]([C:15]2[CH:20]=[CH:19][C:18]([NH:21][CH2:22][CH2:23][OH:24])=[CH:17][CH:16]=2)[CH:10]=[CH:9]3)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 516892Sodium BicarbonateHCID 23019627HCID 23019627, compound

Product 1

HCID 23019633HCID 23019633, compoundYield 10.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

12 mg of ethyl 1-cyclopropyl-9-methyl-4-oxo-8-{4-[2-(tetrahydro-pyran-2-yloxy)-ethylamino]phenyl}-4H-quinolizine-3-carboxylate (Example 21) was dissolved in 1 ml of ethanol. 1 ml of water and 10 mg of pyridinium p-toluenesulfonate were added to the obtained solution, and they were stirred at 50° C. for 9 hours. The reaction mixture was poured into an aqueous sodium hydrogencarbonate solution. After extracting with chloroform, the organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by the silica gel column chromatography (eluent: chloroform/methanol=19/1). 1 ml of ethanol and 1 ml of 1 N sodium hydroxide were added to the obtained crystals, and they were stirred at 50° C. for 2 hours. The reaction mixture was concentrated under reduced pressure and then dissolved in 5 ml of water. The obtained solution was neutralized with 1 N hydrochloric acid. The crystals thus formed were taken by the filtration to obtain 1 mg of 1-cyclopropyl-8-[4-(2-hydroxyethylamino)phenyl]-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid.

Workup

  1. extractionAfter extracting with chloroform
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customThe obtained residue was purified by the silica gel column chromatography (eluent: chloroform/methanol=19/1)
  5. addition1 ml of ethanol and 1 ml of 1 N sodium hydroxide were added to the obtained crystals, and they
  6. stirringwere stirred at 50° C. for 2 hours
  7. concentrationThe reaction mixture was concentrated under reduced pressure
  8. dissolutiondissolved in 5 ml of water
  9. customThe crystals thus formed
  10. filtrationwere taken by the filtration

Sources & evidence

ORD record
ord-57727712a3e3440f926a1bf0dd565d72
Source dataset
uspto-grants-2007_05
Patent number
US07223773B2

Reaction notes

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