Hydrochloric Acid → 2-((7-Fluoro-2-(2-fluorophenyl)-3-methyl-4-quinolinyl)amino)-4-(4-morpholinyl)benzonitrile

HRID 1431247Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1431247
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=2)[N:5]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])[C:3]=1[CH3:20].[NH2:21][C:22]1[CH:29]=[C:28]([N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)[CH:27]=[CH:26][C:23]=1[C:24]#[N:25].Cl.O1CCOCC1>CO>[F:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:21][C:22]3[CH:29]=[C:28]([N:30]4[CH2:31][CH2:32][O:33][CH2:34][CH2:35]4)[CH:27]=[CH:26][C:23]=3[C:24]#[N:25])=[C:3]([CH3:20])[C:4]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[F:19])=[N:5]2)=[CH:10][CH:9]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 134992832-Amino-4-(4-morpholinyl)benzonitrileHCID 596313954-Chloro-7-fluoro-2-(2-fluorophenyl)-3-methylquinoline

Produkt 1

HCID 596315242-((7-Fluoro-2-(2-fluorophenyl)-3-methyl-4-quinolinyl)amino)-4-(4-morpholinyl)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Prepared according to general Procedure K using 4-chloro-7-fluoro-2-(2-fluorophenyl)-3-methylquinoline (70 mg, 0.24 mmol), 2-amino-4-morpholinobenzonitrile (49 mg, 0.24 mmol) and a 4.0M solution of HCl in dioxane (0.030 mL, 0.121 mmol) in MeOH (1.0 mL) and heating in the microwave for 2 h at 150° C. After purification 2-((7-fluoro-2-(2-fluorophenyl)-3-methyl-4-quinolinyl)amino)-4-(4-morpholinyl)benzonitrile was obtained as a yellow film. 1H NMR (500 MHz, chloroform-d) δ ppm 7.94-8.03 (1H, m), 7.82 (1H, dd, J=9.8, 2.7 Hz), 7.60-7.66 (1H, m), 7.43-7.52 (2H, m), 7.32-7.40 (2H, m), 7.13-7.22 (1H, m), 6.56 (1H, br. s.), 6.41 (1H, dd, J=8.8, 2.2 Hz), 5.81 (1H, d, J=2.7 Hz), 3.68-3.77 (4H, m), 2.98-3.15 (4H, m), 2.12-2.26 (3H, s). Mass Spectrum (ESI) m/e=457.0 (M+1).

Aufarbeitung

  1. customPrepared
  2. customAfter purification 2-((7-fluoro-2-(2-fluorophenyl)-3-methyl-4-quinolinyl)amino)-4-(4-morpholinyl)benzonitrile
  3. customwas obtained as a yellow film

Quellen und Nachweise

ORD-Eintrag
ord-945e990b1398496cb0d2c7edc158f29e
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08940724B2

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