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

HRID 2244965

Reaktionsgleichung

Reaktionsgleichung von HRID 2244965
[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

Komponenten

7

Edukt 4

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

Produkt 1

HCID 11684340N-[4-(1-methyl-4,5-dihydro-1H-imidazol-2-yl)phenyl]-2-benzyl-2-(4-chlorophenylaminocarbonylamino)-acetamideAusbeute 40,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-278c96756e55479bbc11c14d05024f6b
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07678913B2

Verknüpfte Notizen

Wird geladen…