Water → HCID 178456932, compound

HRID 1620606

Reaction equation

HRID 1620606 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]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[CH:30][C:29]=1[C:38]([F:41])([F:40])[F:39].O>CN(C=O)C>[F:39][C:38]([F:40])([F:41])[C:29]1[CH:30]=[CH:31][C:32]([C:34]([F:37])([F:35])[F:36])=[CH:33][C:28]=1[CH2:27][N: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

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27731992-(Bromomethyl)-1,4-bis(trifluoromethyl)benzeneHCID 178456897HCID 178456897, compound

Product 1

HCID 178456932HCID 178456932, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of (5Z)-5-(piperidin-4-ylmethylidene)-4-(prop-2-yn-1-ylamino)-1,3-thiazol-2(5H)-one dihydrochloride (200 mg) in DMF (3 mL) was added a solution of potassium carbonate (345 mg) and 2-(bromomethyl)-1,4-bis(trifluoromethyl)benzene (0.129 mL) in DMF (2 mL). The reaction mixture was stirred at room temperature overnight, 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 (156 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-238809cbe59347ae99d4fdda3a8c2c90
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Linked notes

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