Sodium Bicarbonate → HCID 68925447, compound

HRID 1510797Notes

Reaction equation

HRID 1510797 reaction equation
[ClH:1].[O:2]1[C:11]2[CH:10]=[C:9]([CH2:12][NH:13][CH:14]3[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][N:22]4[C:31]5[C:26](=[N:27][C:28]([CH3:33])=[C:29](F)[CH:30]=5)[CH:25]=[CH:24][C:23]4=[O:34])[CH2:16][CH2:15]3)[N:8]=[CH:7][C:6]=2[O:5][CH2:4][CH2:3]1.[C:35](=O)([O-])[OH:36].[Na+]>C(Cl)(Cl)Cl>[ClH:1].[O:2]1[C:11]2[CH:10]=[C:9]([CH2:12][NH:13][CH:14]3[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][N:22]4[C:31]5[C:26](=[N:27][C:28]([CH3:33])=[C:29]([O:36][CH3:35])[CH:30]=5)[CH:25]=[CH:24][C:23]4=[O:34])[CH2:16][CH2:15]3)[N:8]=[CH:7][C:6]=2[O:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 68926892HCID 68926892, compound

Product 1

HCID 68925447HCID 68925447, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 0.16 g of 1-(2-(4-((2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)amino)piperidin-1-yl)ethyl)-7-fluoro-6-methyl-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 dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. To the residue, 2.6 mL of methanol and 0.15 mL of a 28% sodium methoxide/methanol solution were added, and the mixture was heated under reflux while stirring for 2 hours. The reaction mixture was cooled to room temperature, thereto were added chloroform and a saturated aqueous sodium hydrogen carbonate solution, 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 dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. To the resultant residue, 1.4 mL of isopropyl alcohol and 93 μL of concentrated hydrochloric acid were added, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was cooled with ice, and the solid was filtered off to obtain 0.15 g of 1-(2-(4-((2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxy-6-methyl-1,5-naphthyridin-2(1H)-one hydrochloride as a white solid.

Workup

  1. customthe organic layer was separated
  2. extractionthe aqueous layer was extracted with chloroform
  3. dry with materialthe resultant solution was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionTo the residue, 2.6 mL of methanol and 0.15 mL of a 28% sodium methoxide/methanol solution were added
  6. temperaturethe mixture was heated
  7. temperatureunder reflux
  8. additionwere added chloroform
  9. customa saturated aqueous sodium hydrogen carbonate solution, the organic layer was separated
  10. extractionthe aqueous layer was extracted with chloroform
  11. dry with materialthe resultant solution was dried over anhydrous magnesium sulfate
  12. distillationthe solvent was distilled off under reduced pressure
  13. additionTo the resultant residue, 1.4 mL of isopropyl alcohol and 93 μL of concentrated hydrochloric acid were added
  14. stirringthe mixture was stirred at room temperature for 30 minutes
  15. temperatureThe reaction mixture was cooled with ice
  16. filtrationthe solid was filtered off

Sources & evidence

ORD record
ord-a11704c2b58b4b55a367bec4f634c2f6
Source dataset
uspto-grants-2012_07
Patent number
US08211908B2

Reaction notes

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