Hydrochloric Acid → HCID 23139057, compound

HRID 1171677Notes

Reaction equation

HRID 1171677 reaction equation
[ClH:1].Cl.C([S:6][CH:7]1[CH2:12][CH2:11][N:10]([CH:13]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[F:25])[C:14]([CH:16]2[CH2:18][CH2:17]2)=[O:15])[CH2:9]/[C:8]/1=[CH:26]\[C:27]1[N:31]([CH2:32][CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])[N:30]=[N:29][CH:28]=1)(=O)C.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>C(O)C>[ClH:1].[CH:16]1([C:14](=[O:15])[CH:13]([N:10]2[CH2:11][CH2:12][CH:7]([SH:6])/[C:8](=[CH:26]/[C:27]3[N:31]([CH2:32][CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])[N:30]=[N:29][CH:28]=3)/[CH2:9]2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[F:25])[CH2:17][CH2:18]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 516892Sodium Bicarbonate2×HCID 23138767HCID 23138767, compound

Product 1

HCID 23139057HCID 23139057, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrogen chloride was passed through a solution of (E)-4-(acetylsulfanyl)-1-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-3-({1-[3-(ethoxycarbonyl)propyl]-1H-1,2,3-triazol-5-yl}methylidene)piperidine hydrochloride (4.15 g) in ethanol (50 ml) with stirring under ice-cooling for one hour and the resulting mixture was stirred at room temperature overnight under a tightly sealed condition. After concentration of the reaction mixture under reduced pressure, ethyl acetate and an aqueous sodium hydrogencarbonate solution were added to the residue. The organic layer was collected, washed with a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. After evaporation of the solvent under reduced pressure, the residue was purified by silica gel chromatography using hexane and ethyl acetate (1:3) as the eluent, and the crude fraction thus obtained was further purified by preparative HPLC (YMC-Pack ODS-A; YMC, eluent: acetonitrile/0.024 N aqueous hydrochloric acid solution, 40:60, v/v). The fraction obtained was neutralized with an aqueous sodium hydrogencarbonate solution. The resulting free base was extracted with ethyl acetate, and the organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to afford the free base of the title compound (1.93 g, yield: 54%) as a pale yellow oil.

Workup

  1. temperaturecooling for one hour
  2. stirringthe resulting mixture was stirred at room temperature overnight under a tightly sealed condition
  3. customThe organic layer was collected
  4. washwashed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter evaporation of the solvent under reduced pressure
  7. customthe residue was purified by silica gel chromatography
  8. customthe crude fraction thus obtained
  9. customwas further purified by preparative HPLC (YMC-Pack ODS-A
  10. customThe fraction obtained
  11. extractionThe resulting free base was extracted with ethyl acetate
  12. washthe organic layer was washed with a saturated aqueous sodium chloride solution
  13. dry with materialdried over anhydrous magnesium sulfate
  14. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-de23d896aae54e219f38acdadd1ea99c
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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