O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → 2-Amino-N-{4-chloro-3-[5-chloro-1-methyl-6-(3-(trifluoromethyl)piperidin-1-yl)-1H-benzo[d]imidazol-2-ylamino]benzyl}-3,3,3-trifluoro-2-methylpropanamide

HRID 1258631Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1258631
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[NH2:23][C:24]([CH3:32])([C:28]([F:31])([F:30])[F:29])[C:25](O)=[O:26].[Cl:33][C:34]1[CH:41]=[CH:40][C:37]([CH2:38][NH2:39])=[CH:36][C:35]=1[NH:42][C:43]1[N:47]([CH3:48])[C:46]2[CH:49]=[C:50]([N:54]3[CH2:59][CH2:58][CH2:57][CH:56]([C:60]([F:63])([F:62])[F:61])[CH2:55]3)[C:51]([Cl:53])=[CH:52][C:45]=2[N:44]=1>CN(C=O)C>[NH2:23][C:24]([CH3:32])([C:28]([F:31])([F:30])[F:29])[C:25]([NH:39][CH2:38][C:37]1[CH:40]=[CH:41][C:34]([Cl:33])=[C:35]([NH:42][C:43]2[N:47]([CH3:48])[C:46]3[CH:49]=[C:50]([N:54]4[CH2:59][CH2:58][CH2:57][CH:56]([C:60]([F:63])([F:62])[F:61])[CH2:55]4)[C:51]([Cl:53])=[CH:52][C:45]=3[N:44]=2)[CH:36]=1)=[O:26]

Komponenten

5

Edukt 3

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 53117993,3,3-Trifluoro-2-aminoisobutyrateHCID 679582014-Chloro-3-[5-chloro-1-methyl-6-(3-(trifluoromethyl)piperidin-1-yl)-1H-benzo[d]imidazol-2-ylamino]benzylamine

Produkt 1

HCID 866743312-Amino-N-{4-chloro-3-[5-chloro-1-methyl-6-(3-(trifluoromethyl)piperidin-1-yl)-1H-benzo[d]imidazol-2-ylamino]benzyl}-3,3,3-trifluoro-2-methylpropanamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

TBTU (106 mg, 0.3 mmol) followed by TEA (126 μL, 0.9 mmol) were added to 2-amino-3,3,3-trifluoro-2-methylpropanoic acid (57 mg, 0.4 mmol) in DMF (2 mL). After 5 min at rt a mixture of 4-chloro-3-[5-chloro-1-methyl-6-(3-(trifluoromethyl)piperidin-1-yl)-1H-benzo[d]imidazol-2-ylamino]benzylamine (142 mg, 0.3 mmol) and DMF (2 mL) was added to the reaction mixture and stirred at rt overnight. The reaction mixture was purified by chromatography to give the title compound.

Aufarbeitung

  1. additionwas added to the reaction mixture
  2. customThe reaction mixture was purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-2a80c969827341c58785b4583513558d
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08466186B2

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