1,2-Dichloroethane → N-[4-(1-methyl-4,5-dihydro-1H-imidazol-2-yl)phenyl]-2-(2,2-dimethylpropyl)-2-(4-chlorophenylaminocarbonylamino)-acetamide

HRID 2244964Notes

Reaction equation

HRID 2244964 reaction equation
[CH3:1][C:2]([CH3:10])([CH3:9])[CH2:3][C@@H:4]([C:6]([OH:8])=O)[NH2:5].[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]=[C:19]=[O:20])=[CH:14][CH:13]=1.[CH3:21][N:22]1[CH2:26][CH2:25][N:24]=[C:23]1[C:27]1[CH:32]=[CH:31][C:30]([NH2:33])=[CH:29][CH:28]=1.C(Cl)CCl>CN(C=O)C.O>[CH3:21][N:22]1[CH2:26][CH2:25][N:24]=[C:23]1[C:27]1[CH:32]=[CH:31][C:30]([NH:33][C:6](=[O:8])[CH:4]([CH2:3][C:2]([CH3:1])([CH3:10])[CH3:9])[NH:5][C:19]([NH:18][C:15]2[CH:16]=[CH:17][C:12]([Cl:11])=[CH:13][CH:14]=2)=[O:20])=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 76934-Chlorophenyl IsocyanateHCID 194032(2S)-2-Amino-4,4-dimethylpentanoic acidHCID 227288764-(1-Methyl-4,5-dihydro-1H-imidazol-2-yl)-phenylamine

Product 1

HCID 11619441N-[4-(1-methyl-4,5-dihydro-1H-imidazol-2-yl)phenyl]-2-(2,2-dimethylpropyl)-2-(4-chlorophenylaminocarbonylamino)-acetamideYield 51.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of DL-γ-methylleucine (48 mg, 0.33 mmol) in DMF (2 mL), 4-chlorophenyl isocyanate (50 mg, 0.33 mmol) was added. The mixture was then stirred at room temperature overnight. To the reaction mixture, 4-(1-Methyl-4,5-dihydro-1H-imidazol-2-yl)-phenylamine (150 mg, 0.86 mmol) and H2O (0.5 mL, to solubilize the amine) were added. To the solution, EDC (127 mg, 0.66 mmol) was added. After being stirred at room temperature overnight, the solution was concentrated in vacuo. The residue was purified by HPLC to give the titled compound as a powder (77 mg). MS 456.2 and 458.2 (M+H, Cl pattern).

Workup

  1. additionwere added
  2. stirringAfter being stirred at room temperature overnight
  3. concentrationthe solution was concentrated in vacuo
  4. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-a345ab8f0ba0495198f2a0545a6e7e11
Source dataset
uspto-grants-2010_03
Patent number
US07678913B2

Reaction notes

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