Diethyl Ether → Diethyl-[3-(4-{2-isobutyl-4-[4-(4-phenoxy-benzyloxy)-phenyl]-imidazol-1-yl}-phenoxy)-propyl]-amine

HRID 17696Notes

Reaction equation

HRID 17696 reaction equation
[CH2:1]([N:3]([CH2:17][CH3:18])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=1)[CH3:2].C[N:20]([CH:22]=O)C.[CH2:24]([O:31][C:32]1[CH:37]=[CH:36][C:35]([C:38](=O)[CH2:39]Br)=[CH:34][CH:33]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CC[O:44][CH2:45][CH3:46]>O>[CH2:1]([N:3]([CH2:17][CH3:18])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH:39]=[C:38]([C:35]3[CH:36]=[CH:37][C:32]([O:31][CH2:24][C:25]4[CH:30]=[CH:29][C:28]([O:44][C:45]5[CH:46]=[CH:27][CH:26]=[CH:25][CH:24]=5)=[CH:27][CH:26]=4)=[CH:33][CH:34]=3)[N:20]=[C:22]2[CH2:34][CH:35]([CH3:38])[CH3:36])=[CH:10][CH:9]=1)[CH3:2]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6228DimethylformamideHCID 2057886N,N-diethyl-3-(4-nitrophenoxy)propan-1-amineHCID 105425931-[4-(Benzyloxy)phenyl]-2-bromoethan-1-one

Product 1

HCID 59699115Diethyl-[3-(4-{2-isobutyl-4-[4-(4-phenoxy-benzyloxy)-phenyl]-imidazol-1-yl}-phenoxy)-propyl]-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of N,N-diethyl-N-[3-(4-nitrophenoxy)propyl]amine (1.0 eq., 2.5 mmol) in anhydrous DMF (20 mL) DIEA (3 eq) was added, followed by slow addition of the 1-[4-(benzyloxy)phenyl]-2-bromoethanone (2.5 mmol). The reaction mixture was stirred under nitrogen at rt until completion, as indicated by HPLC. The reaction mixture was then diluted with cold H2O and the product was isolated in Et2O. The combined organic layers were washed with brine and dried over sodium sulfate. Evaporation of solvent in vacuuo afforded the desired product. The crude alkylated aniline was purified by chromatography (Silica gel). Pure product was obtained by elution with 2-7% MeOH/DCM (yield˜30%).

Workup

  1. washThe combined organic layers were washed with brine
  2. dry with materialdried over sodium sulfate
  3. customEvaporation of solvent in vacuuo

Sources & evidence

ORD record
ord-ac3884e5fb754cb29adf6fdbabf42f9d
Source dataset
uspto-grants-2010_06
Patent number
US07737285B2

Reaction notes

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