Water → HCID 178459308, compound

HRID 1620543Notes

Reaction equation

HRID 1620543 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:20](=O)([O-])[O-].[K+].[K+].Br[CH2:27][C:28]1[CH:35]=[CH:34][C:31]([C:32]#[N:33])=[CH:30][C:29]=1[C:36]([F:39])([F:38])[F:37].[OH2:40]>CN(C=O)C>[OH:40][C:18]([CH3:20])([CH3:19])[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:35]=[CH:34][C:31]([C:32]#[N:33])=[CH:30][C:29]=2[C:36]([F:39])([F:38])[F:37])[CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 588271604-(bromomethyl)-3-(trifluoromethyl)benzonitrileHCID 178456897HCID 178456897, compound

Product 1

HCID 178459308HCID 178459308, 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 (2 mL) was added a solution of potassium carbonate (312 mg) and 4-(bromomethyl)-3-(trifluoromethyl)benzonitrile (148 mg) in DMF (1 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 (133 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-d746d0cd42254b2c83d5d3a0818de718
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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