Benzylamine → HCID 59333282, compound

HRID 1893487Notes

Reaction equation

HRID 1893487 reaction equation
Br[C:2]1[C:3]([C:16]([F:19])([F:18])[F:17])=[CH:4][C:5]([N+:13]([O-:15])=[O:14])=[C:6]([N:8]2[CH:12]=[CH:11][N:10]=[CH:9]2)[CH:7]=1.[CH2:20]([NH2:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(N(C(C)C)CC)(C)C>C(#N)C>[CH2:20]([NH:27][C:2]1[CH:7]=[C:6]([N:8]2[CH:12]=[CH:11][N:10]=[CH:9]2)[C:5]([N+:13]([O-:15])=[O:14])=[CH:4][C:3]=1[C:16]([F:19])([F:18])[F:17])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 81531DiisopropylethylamineHCID 59333299HCID 59333299, compound

Product 1

HCID 59333282HCID 59333282, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 1-[5-bromo-2-nitro-4-(trifluoromethyl)phenyl]-1H-imidazole (580 mg; 1.73 mmol; 1 eq) prepared as in example 52 step 2, benzylamine (210 μl; 1.9 mmol; 1.1 eq) and diisopropylethylamine (331 μl; 1.9 mmol; 1.1 eq) in anhydrous acetonitrile is stirred at 60° C. for 16 h. Concentration, partition (ethyl acetate/aqueous ammonium chloride), extraction of the aqueous phase (ethyl acetate), reunion of the organic phases, drying (magnesium sulfate), concentration and purification by prep CCM on silicagel (dichloromethane/ethyl acetate 50:50) affords the title product (200 mg; 0.552 mmol; 32%) as a yellow solid.

Workup

  1. concentrationConcentration
  2. custompartition
  3. extraction(ethyl acetate/aqueous ammonium chloride), extraction of the aqueous phase (ethyl acetate), reunion of the organic phases
  4. customdrying
  5. concentration(magnesium sulfate), concentration and purification by prep CCM on silicagel (dichloromethane/ethyl acetate 50:50)

Sources & evidence

ORD record
ord-dbeac1d76587456ca335bf2a8b03e8de
Source dataset
uspto-grants-2013_08
Patent number
US08513250B2

Reaction notes

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