Trifluoroacetic acid → HCID 24947328, compound

HRID 2043333Notes

Reaction equation

HRID 2043333 reaction equation
[N:1]1[CH:5]=[C:4]([CH2:6][NH:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=2)[NH:3][CH:2]=1.CO[C:21]([CH3:23])=[CH2:22].FC(F)(F)C(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCCl>[N:1]1[CH:5]=[C:4]([CH2:6][N:7]([CH:21]([CH3:23])[CH3:22])[C:8]2[CH:9]=[CH:10][C:11]([O:14][C:15]([F:16])([F:17])[F:18])=[CH:12][CH:13]=2)[NH:3][CH:2]=1

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 83002-MethoxypropeneHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 59728120HCID 59728120, compound

Product 1

HCID 24947328HCID 24947328, compoundYield 53.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (3H-imidazol-4-ylmethyl)-(4-trifluoromethoxy-phenyl)-amine (0.39 g, 1.5 mmol) in 1,2-dichloroethane (5 ml) were added successively 2-methoxypropene (0.16 g, 2.25 mmol), trifluoroacetic acid (0.26 g, 2.25 mmol) and sodium triacetoxyborohydride (0.48 g, 2.25 mmol). After stirring the mixture overnight at 60° C. 1 M sodium hydroxide solution (5 ml) was added and the mixture was extracted with dichloromethane. The organic layer was washed with brine, dried over magnesium sulfate and evaporated. The residue was purified by column chromatography (heptane/ethyl acetate=1:1) to yield a white solid (0.24 g, 53%); MS (ISP): 300.1 ((M+H)+.).

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue was purified by column chromatography (heptane/ethyl acetate=1:1)

Sources & evidence

ORD record
ord-5669972d8bf846c586a622189adc9f8d
Source dataset
uspto-grants-2013_11
Patent number
US08586617B2

Reaction notes

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