Hydrochloric Acid → 3-[(7-Chloroquinolin-4-yl)amino]-5-{[2-(piperidin-1-yl)ethyl]amino}benzonitrile

HRID 1190903Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1190903
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([NH:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:9]=1)[C:5]#[N:6].Cl[C:20]1[C:29]2[C:24](=[CH:25][C:26]([Cl:30])=[CH:27][CH:28]=2)[N:23]=[CH:22][CH:21]=1.Cl>C(O)C>[Cl:30][C:26]1[CH:25]=[C:24]2[C:29]([C:20]([NH:1][C:2]3[CH:3]=[C:4]([CH:7]=[C:8]([NH:10][CH2:11][CH2:12][N:13]4[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]4)[CH:9]=3)[C:5]#[N:6])=[CH:21][CH:22]=[N:23]2)=[CH:28][CH:27]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 68664,7-DichloroquinolineHCID 672465403-Amino-5-{[2-(piperidin-1-yl)ethyl]amino}benzonitrile

Produkt 1

HCID 672469973-[(7-Chloroquinolin-4-yl)amino]-5-{[2-(piperidin-1-yl)ethyl]amino}benzonitrileAusbeute 15,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

3-amino-5-{[2-(piperidin-1-yl)ethyl]amino}benzonitrile (200 mg, 0.82 mmol) and 4,7-dichloroquinoline (162 mg, 1 eq) were refluxed in 15 mL of ethanol and 0.82 mL of HCl 1M for 24 h. The reaction mixture was then evaporated and the residue and was purified by preparative thin-layer chromatography (DCM/MeOH/NH4OH//95/5/1) to yield expected compound as a yellow powder (51 mg, 15% yield). m/z (ESI) 406.3 [M+H]+.

Aufarbeitung

  1. customThe reaction mixture was then evaporated
  2. customthe residue and was purified by preparative thin-layer chromatography (DCM/MeOH/NH4OH//95/5/1)

Quellen und Nachweise

ORD-Eintrag
ord-3fc70af493b84577a0e8a8f430104655
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680095B2

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