Trifluoroacetic acid → 2-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-8-(piperidin-4-yl)-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-a]pyridine

HRID 546711Notes

Reaction equation

HRID 546711 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10]1[CH:11]=[C:12](/[CH:22]=[CH:23]/[C:24]2[N:45]=[C:27]3[CH:28]([CH:32]4[CH2:37][CH2:36][N:35](C(OC(C)(C)C)=O)[CH2:34][CH2:33]4)[CH2:29][CH2:30][CH2:31][N:26]3[N:25]=2)[CH:13]=[CH:14][C:15]=1[N:16]1[CH:20]=[C:19]([CH3:21])[N:18]=[CH:17]1.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>C(Cl)Cl>[CH3:8][O:9][C:10]1[CH:11]=[C:12](/[CH:22]=[CH:23]/[C:24]2[N:45]=[C:27]3[CH:28]([CH:32]4[CH2:33][CH2:34][NH:35][CH2:36][CH2:37]4)[CH2:29][CH2:30][CH2:31][N:26]3[N:25]=2)[CH:13]=[CH:14][C:15]=1[N:16]1[CH:20]=[C:19]([CH3:21])[N:18]=[CH:17]1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 66839457tert-butyl 4-(2-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-a]pyridin-8-yl)piperidine-1-carboxylate

Product 1

HCID 668394842-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-8-(piperidin-4-yl)-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-a]pyridineYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1 ml) was added to a solution of tert-butyl 4-(2-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-a]pyridin-8-yl)piperidine-1-carboxylate (361 mg) in methylene chloride (3 ml), and the mixture was stirred at room temperature for two hours. A saturated sodium bicarbonate solution and ethyl acetate were added to the reaction solution, and the organic layer was separated. The organic layer was sequentially washed with a saturated sodium bicarbonate solution and brine. Since most of the target compound was present in the aqueous layers, the combined aqueous layers were extracted with methylene chloride three times. The methylene chloride extraction layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (carrier: Chromatorex™ NH; elution solvent: chloroform-methanol system) to obtain 166 mg of the title compound. The property values of the compound are as follows.

Workup

  1. customthe organic layer was separated
  2. washThe organic layer was sequentially washed with a saturated sodium bicarbonate solution and brine
  3. extractionthe combined aqueous layers were extracted with methylene chloride three times
  4. extractionThe methylene chloride extraction layer
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (carrier: Chromatorex™ NH; elution solvent: chloroform-methanol system)

Sources & evidence

ORD record
ord-208309a8b3a640438e81507a56448e70
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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