Sodium Chloride → HCID 86609485, compound

HRID 1171749Notes

Reaction equation

HRID 1171749 reaction equation
FC(F)(F)C(O)=O.[C:8]([S:11][CH:12]1[CH2:17][CH2:16][NH:15][CH2:14]/[C:13]/1=[CH:18]\[C:19]1[N:20]=[N:21][N:22]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)[CH:23]=1)(=[O:10])[CH3:9].Br[CH:34]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[F:46])[C:35]([CH:37]1[CH2:39][CH2:38]1)=[O:36].C(N(CC)CC)C.[Cl-].[Na+]>C(#N)C>[C:8]([S:11][CH:12]1[CH2:17][CH2:16][N:15]([CH:34]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=2[F:46])[C:35]([CH:37]2[CH2:38][CH2:39]2)=[O:36])[CH2:14]/[C:13]/1=[CH:18]\[C:19]1[N:20]=[N:21][N:22]([CH2:24][C:25]2[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=2)[CH:23]=1)(=[O:10])[CH3:9]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 234358712-Bromo-1-cyclopropyl-2-(2-fluorophenyl)ethan-1-oneHCID 86609486HCID 86609486, compound

Product 1

HCID 86609485HCID 86609485, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (E)-4-(acetylsulfanyl)-3-{[1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl]methylidene}piperidine hydrogen trifluoroacetate (6.03 g) in acetonitrile (100 ml) were added 2-bromo-2-(2-fluorophenyl)-1-cyclopropylethanone (5.0 g) and triethylamine (3.5 ml). The resulting mixture was stirred at room temperature for 15 minutes. Then, the reaction was stopped by addition of a saturated aqueous sodium chloride solution, and the products were extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The residue was purified by chromatography on silica gel using a mixture of hexane, ethyl acetate and dichloromethane (1:1:1) as the eluent to afford the title compound as a pale yellow amorphous solid (5.11 g, yield: 75%).

Workup

  1. extractionthe products were extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe residue was purified by chromatography on silica gel using
  5. additiona mixture of hexane, ethyl acetate and dichloromethane (1:1:1) as the eluent

Sources & evidence

ORD record
ord-b9e8bca261074da1b2d394a08ab4c0fa
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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