Potassium tert-butoxide → HCID 178464054, compound

HRID 1620476Notes

Reaction equation

HRID 1620476 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([CH:12]=O)[CH2:8][CH2:7]1.[CH2:24]([N:26]([CH2:36][CH3:37])[CH2:27][CH2:28][NH:29][C:30]1[CH2:34][S:33][C:32](=[O:35])[N:31]=1)[CH3:25].CC(C)([O-])C.[K+]>C(O)C>[F:23][C:2]([F:1])([F:22])[C:3]1[CH:17]=[C:16]([C:18]([F:20])([F:21])[F:19])[CH:15]=[CH:14][C:4]=1[CH2:5][N:6]1[CH2:7][CH2:8][CH:9](/[CH:12]=[C:34]2/[C:30]([NH:29][CH2:28][CH2:27][N:26]([CH2:36][CH3:37])[CH2:24][CH3:25])=[N:31][C:32](=[O:35])[S:33]/2)[CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 23665647Potassium tert-butoxideHCID 866786631-[2,4-Bis(trifluoromethyl)benzyl]piperidine-4-carbaldehydeHCID 178464053HCID 178464053, compound

Product 1

HCID 178464054HCID 178464054, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1-[2,4-bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde (6.64 g) and 4-{[2-(diethylamino)ethyl]amino}-1,3-thiazol-2(5H)-one (5.48 g) in ethanol (98 mL) was added potassium tert-butoxide (2.85 g). The reaction mixture was stirred at 80° C. for 20 min, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane). The solvent was evaporated under reduced pressure, the residue was dissolved in ethyl acetate, the solution 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 (NH, methanol/ethyl acetate) and further silica gel column chromatography (methanol/ethyl acetate) to give the title compound (7.84 g).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)
  3. customThe solvent was evaporated under reduced pressure
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washthe solution was washed with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate) and further silica gel column chromatography (methanol/ethyl acetate)

Sources & evidence

ORD record
ord-4440e8c9393b456984e75e56298fcd66
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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