Hydrochloric Acid → HCID 23564777, compound

HRID 1059367Notes

Reaction equation

HRID 1059367 reaction equation
COC[N:4]1[C:9]2[CH:10]=[C:11]([CH2:14][CH2:15][CH:16]=O)[CH:12]=[CH:13][C:8]=2[S:7][C:6]2[N:18]=[CH:19][CH:20]=[N:21][C:5]1=2.[NH:22]1[CH2:32][CH2:31][CH:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:24][CH2:23]1.[C-]#N.[BH4-].[Na+].[OH-].[Na+].Cl.C(=O)(O)[O-].[Na+]>C(#N)C.O1CCCC1.C(O)(=O)C>[CH2:29]([O:28][C:26]([CH:25]1[CH2:31][CH2:32][N:22]([CH2:16][CH2:15][CH2:14][C:11]2[CH:12]=[CH:13][C:8]3[S:7][C:6]4[N:18]=[CH:19][CH:20]=[N:21][C:5]=4[NH:4][C:9]=3[CH:10]=2)[CH2:23][CH2:24]1)=[O:27])[CH3:30]

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 70770Ethyl 4-piperidinecarboxylateHCID 516892Sodium BicarbonateHCID 18670526HCID 18670526, compoundHCID 131723130HCID 131723130, compound

Product 1

HCID 23564777HCID 23564777, compoundYield 49.6%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.6 g of 3-[10-(methoxymethyl)-10H-pyrazino[2,3-b][1,4]benzothiazin-8-yl]propionaldehyde and 0.31 g of ethyl isonipecotate in acetonitrile (50 ml) was added 0.2 g of sodium borohydride cyanide. Further, acetic acid was added so as to maintain the pH value at 4. Then the resulting mixture was reacted at room temperature for 12 hours. After adding an aqueous solution of sodium hydroxide, the reaction mixture was extracted with ethyl acetate, washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the crude product thus obtained was dissolved in 30 ml of tetrahydrofuran. After adding 1 ml of 6 N hydrochloric acid, the resulting mixture was reacted for 1 hour. After adding an aqueous solution of sodium bicarbonate, the reaction mixture was extracted with ethyl acetate, washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluted with methanol/dichloromethane) to thereby give 0.39 g of the title compound as a brown oily substance.

Workup

  1. temperatureto maintain the pH value at 4
  2. customThen the resulting mixture was reacted at room temperature for 12 hours
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washwashed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationAfter distilling off the solvent under reduced pressure
  7. customthe crude product thus obtained
  8. customthe resulting mixture was reacted for 1 hour
  9. extractionthe reaction mixture was extracted with ethyl acetate
  10. washwashed with a saturated aqueous solution of sodium chloride
  11. dry with materialdried over anhydrous magnesium sulfate
  12. distillationAfter distilling off the solvent under reduced pressure
  13. customthe residue was purified by silica gel column chromatography (eluted with methanol/dichloromethane)

Sources & evidence

ORD record
ord-99641b700fab4354bf93e1f56413ba17
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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