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

HRID 2244965

Reaction equation

HRID 2244965 reaction equation
[NH2:1][CH:2]([C:10]([OH:12])=O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]=[C:21]=[O:22])=[CH:16][CH:15]=1.[CH3:23][N:24]1[CH2:28][CH2:27][N:26]=[C:25]1[C:29]1[CH:34]=[CH:33][C:32]([NH2:35])=[CH:31][CH:30]=1.C(Cl)CCl>CN(C=O)C.O>[CH3:23][N:24]1[CH2:28][CH2:27][N:26]=[C:25]1[C:29]1[CH:34]=[CH:33][C:32]([NH:35][C:10](=[O:12])[CH:2]([CH2:3][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:1][C:21]([NH:20][C:17]2[CH:18]=[CH:19][C:14]([Cl:13])=[CH:15][CH:16]=2)=[O:22])=[CH:31][CH:30]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 994Dl-PhenylalanineHCID 76934-Chlorophenyl IsocyanateHCID 227288764-(1-Methyl-4,5-dihydro-1H-imidazol-2-yl)-phenylamine

Product 1

HCID 11684340N-[4-(1-methyl-4,5-dihydro-1H-imidazol-2-yl)phenyl]-2-benzyl-2-(4-chlorophenylaminocarbonylamino)-acetamideYield 40.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of DL-phenylalanine (83 mg, 0.50 mmol) in DMF (6 mL), 4-chlorophenyl isocyanate (77 mg, 0.50 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 (180 mg, 1.02 mmol) and H2O (1 mL, to solubilize the amine) were added. To the solution, EDC (200 mg, 1.04 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 (96 mg). MS 476.1 and 478.1 (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-278c96756e55479bbc11c14d05024f6b
Source dataset
uspto-grants-2010_03
Patent number
US07678913B2

Linked notes

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