1-Hydroxybenzotriazole → N-[1-amino(3,5-dimethyl-1H-pyrazol-1-yl)methylene]-4-(2,4,6-trifluorophenyl)quinoline-6-carboxamide

HRID 533395

Reaktionsgleichung

Reaktionsgleichung von HRID 533395
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=1[C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20](O)=[O:21])[CH:18]=2)[N:13]=[CH:12][CH:11]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[N+]([O-])(O)=O.[CH3:49][C:50]1[CH:54]=[C:53]([CH3:55])[N:52]([C:56](=[NH:58])[NH2:57])[N:51]=1.CCN(C(C)C)C(C)C>O.CN(C=O)C>[NH2:58][C:56]([N:52]1[C:53]([CH3:55])=[CH:54][C:50]([CH3:49])=[N:51]1)=[N:57][C:20]([C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[N:13]=[CH:12][CH:11]=[C:10]2[C:3]1[C:2]([F:1])=[CH:7][C:6]([F:8])=[CH:5][C:4]=1[F:9])=[O:21]

Komponenten

8

Edukt 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1981863,5-Dimethyl-1H-pyrazole-1-carboxamidine mononitrateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 677759694-(2,4,6-Trifluorophenyl)quinoline-6-carboxylic acid

Produkt 1

HCID 67774710N-[1-amino(3,5-dimethyl-1H-pyrazol-1-yl)methylene]-4-(2,4,6-trifluorophenyl)quinoline-6-carboxamideAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 4-(2,4,6-trifluorophenyl)quinoline-6-carboxylic acid (118 mg), WSC hydrochloride (112 mg), HOBt (37 mg), and DMF (4 mL) was stirred at room temperature for 5 minutes, and then 3,5-dimethyl-1H-pyrazole-1-carboximidamide nitrate (94 mg) and DIPEA (76 mg) were added thereto, followed by stirring for an additional 24 hours. The reaction mixture was diluted with water, and the precipitate was collected by filtration to obtain N-[1-amino(3,5-dimethyl-1H-pyrazol-1-yl)methylene]-4-(2,4,6-trifluorophenyl)quinoline-6-carboxamide (140 mg).

Aufarbeitung

  1. stirringby stirring for an additional 24 hours
  2. filtrationthe precipitate was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-307778821b1a40cc925d19ba7f9edaed
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853242B2

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