Hydrochloric Acid → N-(2-methyl-1H-indol-5-yl)-7-(trifluoromethyl)quinolin-4-amine

HRID 130656

Reaktionsgleichung

Reaktionsgleichung von HRID 130656
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[CH3:16][C:17]1[NH:18][C:19]2[C:24]([CH:25]=1)=[CH:23][C:22]([NH2:26])=[CH:21][CH:20]=2.Cl.O1CCOCC1.CCO.ClC(Cl)C>>[CH3:16][C:17]1[NH:18][C:19]2[C:24]([CH:25]=1)=[CH:23][C:22]([NH:26][C:2]1[C:11]3[C:6](=[CH:7][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:9][CH:10]=3)[N:5]=[CH:4][CH:3]=1)=[CH:21][CH:20]=2

Komponenten

6

Edukt 5

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 676684-Chloro-7-(trifluoromethyl)quinolineHCID 27339925-Amino-2-methylindoleHCID 18381953Dichloroethane ethanol

Produkt 1

HCID 59730772N-(2-methyl-1H-indol-5-yl)-7-(trifluoromethyl)quinolin-4-amineAusbeute 17,2 %

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A suspension of 4-chloro-7-(trifluoromethyl)quinoline 1-A (158 mg, 0.68 mmol), 2-methyl-1H-indol-5-amine 1-B (100 mg, 0.68 mmol) and 4N HCl in dioxane (0.25 ml, 1.0 mmol) in a mix solvent (EtOH/dichloroethane, 1:1, 6 ml) was heated to 90° C. in a sealed tube overnight. The reaction mixture was concentrated and dissolved in 2 ml of DMSO. The solution was purified by HPLC (DionexSystem, 20-60% CH3CN/H2O over 30 minutes). 40 mg of N-(2-methyl-1H-indol-5-yl)-7-(trifluoromethyl)quinolin-4-amine 1 was obtained.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. dissolutiondissolved in 2 ml of DMSO
  3. customThe solution was purified by HPLC (DionexSystem, 20-60% CH3CN/H2O over 30 minutes)

Quellen und Nachweise

ORD-Eintrag
ord-97edca1ff174403b8d5ac887663ba404
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07381824B2

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