1,2-Dichloroethane → 1-(4-Cyanobenzyl)-5-(4'-phenylbenzamido)ethyl-imidazole

HRID 1422333Notes

Reaction equation

HRID 1422333 reaction equation
[C:1]([C:3]1[CH:17]=[CH:16][C:6]([CH2:7][N:8]2[C:12]([CH2:13][CH2:14][NH2:15])=[CH:11][N:10]=[CH:9]2)=[CH:5][CH:4]=1)#[N:2].[C:18]1([C:24]2[CH:32]=[CH:31][C:27]([C:28](O)=[O:29])=[CH:26][CH:25]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.ON1C(=O)C2C=CC=CC=2N=N1.C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC.C(Cl)CCl>CN(C=O)C>[C:1]([C:3]1[CH:17]=[CH:16][C:6]([CH2:7][N:8]2[C:12]([CH2:13][CH2:14][NH:15][C:28](=[O:29])[C:27]3[CH:31]=[CH:32][C:24]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:25][CH:26]=3)=[CH:11][N:10]=[CH:9]2)=[CH:5][CH:4]=1)#[N:2]

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 66724(1,1'-Biphenyl)-4-carboxylic acidHCID 730263-hydroxy-1,2,3-benzotriazin-4(3H)-oneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 158510473-(4-Cyanobenzyl) histamine

Product 1

HCID 544094141-(4-Cyanobenzyl)-5-(4'-phenylbenzamido)ethyl-imidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(4-cyanobenzyl)-5-aminoethylimidazole (107 mg, 0.358 mmol), 4-phenylbenzoic acid (70.9 mg, 0.358 mmol), 3-hydroxy-1,2,3-benzotriazin-4(3H)-one, (72.6 mg, 0.445 mmol) and triethylamine (0.215 mL, 1.54 mmol) in DMF (4.0 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, EDC, (83.3 mg, 0.435 mmol) and the mixture stirred for 16 hours at ambient temperature. The reaction was partitioned between sat. aq. NaHCO3 solution and EtOAc. The organic layer was dried, (Na2SO4) and the solvent evaporated in vacuo. The residue was chromatographed (Silica gel, 5% MeOH in CH2Cl2) to afford the imidazole which was converted to the HCl salt by treatment with one equivalent of HCl in aqueous acetonitrile. Evaporation of the solvent in vacuo afforded the title compound as a white solid.

Workup

  1. customThe reaction was partitioned between sat. aq. NaHCO3 solution and EtOAc
  2. customThe organic layer was dried
  3. custom(Na2SO4) and the solvent evaporated in vacuo
  4. customThe residue was chromatographed (Silica gel, 5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-d3d37059eecd47819ee2f0320df2ebad
Source dataset
uspto-grants-2000_06
Patent number
US06080870

Reaction notes

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