Water → HCID 178456909, compound

HRID 1620519Notes

Reaction equation

HRID 1620519 reaction equation
Cl.Cl.[NH:3]1[CH2:8][CH2:7][CH:6](/[CH:9]=[C:10]2/[C:11]([NH:16][CH2:17][C:18]#[CH:19])=[N:12][C:13](=[O:15])[S:14]/2)[CH2:5][CH2:4]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[CH:29]=1.O>CN(C=O)C>[CH2:17]([NH:16][C:11]1=[N:12][C:13](=[O:15])[S:14]/[C:10]/1=[CH:9]\[CH:6]1[CH2:7][CH2:8][N:3]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:35])([F:36])[F:37])[CH:29]=2)[CH2:4][CH2:5]1)[C:18]#[CH:19]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1230611-(Bromomethyl)-3-(trifluoromethyl)benzeneHCID 178456897HCID 178456897, compound

Product 1

HCID 178456909HCID 178456909, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (5Z)-5-(piperidin-4-ylmethylidene)-4-(prop-2-yn-1-ylamino)-1,3-thiazol-2(5H)-one dihydrochloride (300 mg) in DMF (3 mL) were added potassium carbonate (517 mg) and 1-(bromomethyl)-3-(trifluoromethyl)benzene (0.15 mL). The reaction mixture was stirred at room temperature for 4 hr, water was added, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) and recrystallized from ethyl acetate/heptane to give the title compound (64 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
  6. customrecrystallized from ethyl acetate/heptane

Sources & evidence

ORD record
ord-030d07ae4c534b94b0d7979240c5ab30
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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