Sodium Chloride → HCID 86609425, compound

HRID 1171670Notes

Reaction equation

HRID 1171670 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:23]([CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])[N:22]=[N:21][CH:20]=1)(=[O:10])[CH3:9].Br[CH:31]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[F:43])[C:32]([CH:34]1[CH2:36][CH2:35]1)=[O:33].C(N(CC)CC)C.[Cl-:51].[Na+]>C(#N)C>[ClH:51].[C:8]([S:11][CH:12]1[CH2:17][CH2:16][N:15]([CH:31]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=2[F:43])[C:32]([CH:34]2[CH2:35][CH2:36]2)=[O:33])[CH2:14]/[C:13]/1=[CH:18]\[C:19]1[N:23]([CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])[N:22]=[N:21][CH:20]=1)(=[O:10])[CH3:9]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 234358712-Bromo-1-cyclopropyl-2-(2-fluorophenyl)ethan-1-oneHCID 86609427HCID 86609427, compound

Product 1

HCID 86609425HCID 86609425, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (E)-4-(acetylsulfanyl)-3-({1-[2-(methoxycarbonyl)ethyl]-1H-1,2,3-triazol-5-yl}methylidene)piperidine hydrogen trifluoroacetate (3.5 g) in acetonitrile (100 ml) were added 2-bromo-2-(2-fluorophenyl)-1-cyclopropylethanone (4.1 g) and triethylamine (3.3 ml), and the resulting mixture was stirred at room temperature for 15 minutes. After addition of aqueous sodium chloride solution, products was extracted with ethyl acetate. The extract was washed with a saturated aqueous sodium chloride solution and the organic layer was dried over anhydrous magnesium sulfate. After evaporation of the solvent under reduced pressure, the residue was purified by silica gel chromatography using hexane, ethyl acetate, and dichloromethane (1:2:1) as the eluent to afford a free base of the title compound (1.97 g) as a pale yellow amorphous solid.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe extract was washed with a saturated aqueous sodium chloride solution
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. customAfter evaporation of the solvent under reduced pressure
  5. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-88989363ae524568ade84d58e1cabecb
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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