Trifluoroacetic acid → HCID 58243781, compound

HRID 389159Notes

Reaction equation

HRID 389159 reaction equation
[CH3:1][C:2]([O:8][C:9]1[C:14]([F:15])=[CH:13][C:12]([F:16])=[CH:11][C:10]=1[F:17])([CH3:7])[C:3]([NH:5][NH2:6])=O.FC(F)(F)C(O)=O.[CH2:25]([N:27]=[C:28](SC)[N:29]1[CH2:34][CH2:33][CH:32]([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:31][CH2:30]1)[CH3:26].C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[CH2:25]([N:27]1[C:3]([C:2]([CH3:7])([O:8][C:9]2[C:14]([F:15])=[CH:13][C:12]([F:16])=[CH:11][C:10]=2[F:17])[CH3:1])=[N:5][N:6]=[C:28]1[N:29]1[CH2:30][CH2:31][CH:32]([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:33][CH2:34]1)[CH3:26]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 58243583HCID 58243583, compoundHCID 58243616HCID 58243616, compound

Product 1

HCID 58243781HCID 58243781, compoundYield 28.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

2-methyl-2-(2,4,6-trifluorophenoxy)propanohydrazide (500 mg) and trifluoroacetic acid (0.08 ml) were added to a solution of ethyl 1-[(ethylimino)(methylsulfanyl)methyl]piperidine-4-carboxylate (600 mg) in toluene (10 ml), followed by stirring at 120° C. for 8 hours. An aqueous saturated sodium hydrogen carbonate solution was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate and the solvent was then evaporated. The resulting residue was purified by silica gel column chromatography (using basic silica:hexane:ethyl acetate=100:0 to 50:50 to 0:100) to obtain ethyl 1-{4-ethyl-5-[1-methyl-1-(2,4,6-trifluorophenoxy)ethyl]-4H-1,2,4-triazol-3-yl}piperidine-4-carboxylate (254 mg), as a colorless solid.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was then evaporated
  5. customThe resulting residue was purified by silica gel column chromatography (using basic silica:hexane:ethyl acetate=100:0 to 50:50 to 0:100)

Sources & evidence

ORD record
ord-8c818e0387ab437bbd6263218148b9fd
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Reaction notes

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