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

HRID 2244963

Reaction equation

HRID 2244963 reaction equation
[NH2:1][CH:2]([C:7]([OH:9])=O)[C:3]([CH3:6])([CH3:5])[CH3:4].[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]=[C:18]=[O:19])=[CH:13][CH:12]=1.[CH3:20][N:21]1[CH2:25][CH2:24][N:23]=[C:22]1[C:26]1[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][CH:27]=1.C(Cl)CCl>CN(C=O)C.O>[CH3:20][N:21]1[CH2:25][CH2:24][N:23]=[C:22]1[C:26]1[CH:31]=[CH:30][C:29]([NH:32][C:7](=[O:9])[CH:2]([C:3]([CH3:6])([CH3:5])[CH3:4])[NH:1][C:18]([NH:17][C:14]2[CH:15]=[CH:16][C:11]([Cl:10])=[CH:12][CH:13]=2)=[O:19])=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 76934-Chlorophenyl IsocyanateHCID 3061312-Amino-3,3-dimethylbutanoic acidHCID 227288764-(1-Methyl-4,5-dihydro-1H-imidazol-2-yl)-phenylamine

Product 1

HCID 11546712N-[4-(1-methyl-4,5-dihydro-1H-imidazol-2-yl)phenyl]-2-(1,1-dimethylethyl)-2-(4-chlorophenylaminocarbonylamino)-acetamideYield 24%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of DL-tert-leucine (43 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 (35 mg). MS 442.1 and 444.1 (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-0dcef1a7a5ff4d948de1d9ca9bc7c4e7
Source dataset
uspto-grants-2010_03
Patent number
US07678913B2

Linked notes

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