O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → N-[4-Methoxy-3-(4-bromophenyl)aminocarbonyl-phenyl]-2-chloro-5-(tert-butylcarbonylamino)methyl-benzamide

HRID 1846083Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1846083
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[Cl:23][C:24]1[CH:32]=[CH:31][C:30]([CH2:33][NH:34][C:35]([C:37]([CH3:40])([CH3:39])[CH3:38])=[O:36])=[CH:29][C:25]=1[C:26]([OH:28])=O.[Br:41][C:42]1[CH:47]=[CH:46][C:45]([NH:48][C:49](=[O:59])[C:50]2[CH:55]=[C:54]([NH2:56])[CH:53]=[CH:52][C:51]=2[O:57][CH3:58])=[CH:44][CH:43]=1>CN(C=O)C>[CH3:58][O:57][C:51]1[CH:52]=[CH:53][C:54]([NH:56][C:26](=[O:28])[C:25]2[CH:29]=[C:30]([CH2:33][NH:34][C:35]([C:37]([CH3:40])([CH3:39])[CH3:38])=[O:36])[CH:31]=[CH:32][C:24]=2[Cl:23])=[CH:55][C:50]=1[C:49]([NH:48][C:45]1[CH:46]=[CH:47][C:42]([Br:41])=[CH:43][CH:44]=1)=[O:59]

Komponenten

5

Edukt 3

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 584832082-Chloro-5-[(2,2-dimethylpropanamido)methyl]benzoic acidHCID 61090759N-(4-Bromophenyl)-2-methoxy-5-amino-benzoic acid amide

Produkt 1

HCID 51347356N-[4-Methoxy-3-(4-bromophenyl)aminocarbonyl-phenyl]-2-chloro-5-(tert-butylcarbonylamino)methyl-benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

TBTU (40 mg, 0.125 mmol) in 0.25 mL DMF was added to 2-chloro-5-(tert-butylcarbonylamino)methyl-benzoic acid (34 mg, 0.125 mmol), followed by 50 μL TEA and the mixture was stirred for 5 min. Then N-(4-bromophenyl)-2-methoxy-5-amino-benzoic acid amide in 0.25 mL DMF was added and it was stirred overnight. The crude mixture was filtered through aluminium oxide and the solid phase was washed 4× with 1 mL DMF/MeOH 9:1. The combined organic phase was concentrated i.vac. dissolved in Acetonitrile/HCOOH, filtered and dried via lyophilisation to furnish the title compound.

Aufarbeitung

  1. stirringit was stirred overnight
  2. filtrationThe crude mixture was filtered through aluminium oxide
  3. washthe solid phase was washed 4× with 1 mL DMF/MeOH 9:1
  4. concentrationThe combined organic phase was concentrated i.vac
  5. dissolutiondissolved in Acetonitrile/HCOOH
  6. filtrationfiltered
  7. customdried via lyophilisation

Quellen und Nachweise

ORD-Eintrag
ord-3a065fc8e86647b995c48bfb875bb2f1
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08951999B2

Notizen zur Reaktion

Wird geladen…