4-Amino-3-methylbenzonitrile → 2-Bromo-5-[(4-chloro-phenyl)-(4-cyano-2-methyl-phenylamino)-methyl]-1-isopropyl-1H-imidazole-4-carboxylic acid

HRID 2410121Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2410121
C([O:3][C:4]([C:6]1[N:7]=[C:8]([Br:23])[N:9]([CH:20]([CH3:22])[CH3:21])[C:10]=1[CH:11]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)O)=[O:5])C.[NH2:24][C:25]1[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][C:26]=1[CH3:33]>>[Br:23][C:8]1[N:9]([CH:20]([CH3:21])[CH3:22])[C:10]([CH:11]([C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)[NH:24][C:25]2[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][C:26]=2[CH3:33])=[C:6]([C:4]([OH:3])=[O:5])[N:7]=1

Komponenten

3

Edukt 2

HCID 70103164-Amino-3-methylbenzonitrileHCID 86707749ethyl 2-bromo-5-((4-chlorophenyl)(hydroxy)methyl)-1-isopropyl-1H-imidazole-4-carboxylate

Produkt 1

HCID 867077742-Bromo-5-[(4-chloro-phenyl)-(4-cyano-2-methyl-phenylamino)-methyl]-1-isopropyl-1H-imidazole-4-carboxylic acid

Versuchsvorschrift

The title compound was prepared in analogy to the procedure described for step E2 but using intermediate B and 4-amino-3-methylbenzonitrile. The reaction mixture was stirred at rt for 20 h. The mixture was extracted with HCl 1M and with a saturated aqueous NaHCO3 solution. The organic layers were dried (Na2SO4), filtered and concentrated. The product was triturated in Et2O, the suspension was filtered and the solid was dried in HV. tR: 1.30 min (LC-MS 2); ESI-MS: 515.2/517.1 [M+H]+ (LC-MS 2).

Aufarbeitung

  1. extractionThe mixture was extracted with HCl 1M and with a saturated aqueous NaHCO3 solution
  2. dry with materialThe organic layers were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe product was triturated in Et2O
  6. filtrationthe suspension was filtered
  7. customthe solid was dried in HV

Quellen und Nachweise

ORD-Eintrag
ord-b05e6679e7774be8a4a529bd69d3fd06
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08815926B2

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