Sodium Bicarbonate → HCID 57815412, compound

HRID 385669Notes

Reaction equation

HRID 385669 reaction equation
Cl.[O:2]1[C:12]2[CH:11]=[C:10]([CH2:13][NH:14][CH:15]3[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][N:23]4[C:32]5[C:27](=[N:28][CH:29]=[C:30](F)[CH:31]=5)[CH:26]=[CH:25][C:24]4=[O:34])[CH2:17][CH2:16]3)[N:9]=[CH:8][C:7]=2[O:6][CH2:5][CH2:4][CH2:3]1.[C:35](=O)([O-])[OH:36].[Na+]>C(Cl)(Cl)Cl>[O:2]1[C:12]2[CH:11]=[C:10]([CH2:13][NH:14][CH:15]3[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][N:23]4[C:32]5[C:27](=[N:28][CH:29]=[C:30]([O:36][CH3:35])[CH:31]=5)[CH:26]=[CH:25][C:24]4=[O:34])[CH2:17][CH2:16]3)[N:9]=[CH:8][C:7]=2[O:6][CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 68932494HCID 68932494, compound

Product 1

HCID 57815412HCID 57815412, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 85 mg of 1-(2-(4-((3,4-dihydro-2H-(1,4)dioxepino(2,3-c)pyridin-8-ylmethyl)amino)piperidin-1-yl)ethyl)-7-fluoro-1,5-naphthyridin-2(1H)-one hydrochloride, chloroform and a saturated aqueous sodium hydrogen carbonate solution were added, the organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and the extract were combined, the resultant solution was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. To the resultant oily substance, 2 mL of methanol and 83 mg of a 28% sodium methoxide/methanol solution were added at room temperature, and the mixture was heated under reflux while stirring for 4 hours. After cooling to room temperature, water and chloroform were added to the reaction mixture, the organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and the extract were combined, the resultant residue was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 53 mg of 1-(2-(4-((3,4-dihydro-2H-(1,4)dioxepino(2,3-c)pyridin-8-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxy-1,5-naphthyridin-2(1H)-one as a light brown oily substance.

Workup

  1. customthe organic layer was separated
  2. extractionthe aqueous layer was extracted with chloroform
  3. washthe resultant solution was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. additionTo the resultant oily substance, 2 mL of methanol and 83 mg of a 28% sodium methoxide/methanol solution were added at room temperature
  7. temperaturethe mixture was heated
  8. temperatureunder reflux
  9. additionwater and chloroform were added to the reaction mixture
  10. customthe organic layer was separated
  11. extractionthe aqueous layer was extracted with chloroform
  12. washthe resultant residue was washed with a saturated aqueous sodium chloride solution
  13. dry with materialdried over anhydrous magnesium sulfate
  14. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-7dba326ca0834418b35090b79c5d9dbe
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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