Hydrochloric Acid → HCID 23138827, compound

HRID 1171726Notes

Reaction equation

HRID 1171726 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:28]([CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH:29]=[CH:30][N:31]=1)(=O)C>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:28]([CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH:29]=[CH:30][N:31]=3)/[CH2:9]2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[F:25])[CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 23138616HCID 23138616, compound

Product 1

HCID 23138827HCID 23138827, compoundYield 47%

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-(ethoxycarbonylmethyl)-1H-imidazol-2-yl]methylidene}piperidine hydrochloride (169.4 mg) in ethanol (4 ml) at 0° C. and the sealed mixture was stirred at room temperature for 6.5 hours. The mixture was concentrated under reduced pressure and the residue was purified by preparative HPLC (YMC-Pack ODS-A; YMC, eluent: acetonitrile/0.026 N aqueous trifluoroacetic acid solution, 25/75, v/v). The thus obtained trifluoroacetic acid salt of the title compound was neutralized with an aqueous sodium hydrogen carbonate solution, and the liberated free base was extracted twice with dichloromethane. The extract was dried over anhydrous sodium sulfate and solvents were removed under reduced pressure to afford the free base of the title compound (67.7 mg, yield: 47%) as a colourless oil. The oil thus obtained was treated with a 4N hydrogen chloride dioxane solution (120 μl) in acetonitrile (3 ml). The solvent and excess hydrogen chloride were removed by evaporation under reduced pressure to afford the title compound (88.9 mg) as a pale yellow amorphous solid.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was purified by preparative HPLC (YMC-Pack ODS-A
  3. extractionthe liberated free base was extracted twice with dichloromethane
  4. dry with materialThe extract was dried over anhydrous sodium sulfate and solvents
  5. customwere removed under reduced pressure

Sources & evidence

ORD record
ord-cf40a459a42141ae9c48d657d0802a65
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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