Acetonitrile → HCID 23138622, compound

HRID 1171683Notes

Reaction equation

HRID 1171683 reaction equation
C(=O)([O-])[O-].[K+].[K+].[ClH:7].C([S:11][CH:12]1[CH2:17][CH2:16][N:15]([CH:18]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[F:30])[C:19]([CH:21]2[CH2:23][CH2:22]2)=[O:20])[CH2:14]/[C:13]/1=[CH:31]\[C:32]1[N:33]=[N:34][N:35]([CH2:37][C:38]([O:40][CH3:41])=[O:39])[N:36]=1)(=O)C.C(#N)C>CO.C(OCC)(=O)C>[ClH:7].[CH:21]1([C:19](=[O:20])[CH:18]([N:15]2[CH2:16][CH2:17][CH:12]([SH:11])/[C:13](=[CH:31]/[C:32]3[N:33]=[N:34][N:35]([CH2:37][C:38]([O:40][CH3:41])=[O:39])[N:36]=3)/[CH2:14]2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[F:30])[CH2:23][CH2:22]1

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 86609432HCID 86609432, compound

Product 1

HCID 23138622HCID 23138622, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium carbonate (275 mg) was added to a solution of (E)-4-(acetylsulfanyl)-1-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-3-{[2-(methoxycarbonylmethyl)-2H-tetrazol-5-yl]methylidene}piperidine hydrochloride (347 mg) in methanol (10 ml). After being stirred at room temperature for 15 minutes, the mixture was diluted with ethyl acetate, and the reaction was quenched by addition of water. The organic layer was separated, washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. Removal of the solvent under reduced pressure followed by purification of the residue by preparative HPLC (YMC-Pack ODS-A; YMC, eluent: acetonitrile/0.024 N hydrochloric acid, 35/65, v/v) to afford the title compound (185 mg, yield: 58%) as a colourless amorphous solid.

Workup

  1. customthe reaction was quenched by addition of water
  2. customThe organic layer was separated
  3. washwashed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customRemoval of the solvent under reduced pressure
  6. customfollowed by purification of the residue by preparative HPLC (YMC-Pack ODS-A

Sources & evidence

ORD record
ord-a14770bfb6c047f5a76fa1f07418bd77
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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