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

HRID 1431248Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1431248
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:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[C:3]=1[CH3:19].[NH2:20][C:21]1[CH:28]=[C:27]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)[CH:26]=[CH:25][C:22]=1[C:23]#[N:24].Cl.O1CCOCC1>CN1C(=O)CCC1>[F:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:20][C:21]3[CH:28]=[C:27]([N:29]4[CH2:30][CH2:31][O:32][CH2:33][CH2:34]4)[CH:26]=[CH:25][C:22]=3[C:23]#[N:24])=[C:3]([CH3:19])[C:4]([C:13]3[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=3)=[N:5]2)=[CH:10][CH:9]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 134992832-Amino-4-(4-morpholinyl)benzonitrileHCID 596310524-Chloro-7-fluoro-3-methyl-2-(pyridin-3-yl)quinoline

Produkt 1

HCID 509052822-((7-Fluoro-3-methyl-2-(3-pyridinyl)-4-quinolinyl)amino)-4-(4-morpholinyl)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

Prepared according to general Procedure K using 4-chloro-7-fluoro-3-methyl-2-(pyridin-3-yl)quinoline (150 mg, 0.55 mmol), 2-amino-4-morpholinobenzonitrile (112 mg, 0.55 mmol) and a 4.0M solution of HCl in dioxane (0.028 mL, 0.11 mmol) in NMP (1.0 mL) and heating in the microwave for 2 h at 150° C. After purification 2-((7-fluoro-3-methyl-2-(3-pyridinyl)-4-quinolinyl)amino)-4-(4-morpholinyl)benzonitrile was obtained as a yellow film. 1H NMR (500 MHz, chloroform-d) δ ppm 8.87 (1H, dd, J=2.0, 0.5 Hz), 8.73 (1H, dd, J=4.9, 1.7 Hz), 7.99 (1H, dt, J=7.8, 2.0 Hz), 7.92 (1H, dd, J=9.3, 5.9 Hz), 7.80 (1H, dd, J=9.8, 2.4 Hz), 7.44-7.51 (2H, m), 7.33 (1H, ddd, J=9.2, 8.0, 2.6 Hz), 6.46 (1H, s), 6.43 (1H, dd, J=8.9, 2.3 Hz), 5.72 (1H, d, J=2.2 Hz), 3.63-3.76 (4H, m), 2.95-3.09 (4H, m), 2.35 (3H, s). Mass Spectrum (ESI) m/e=440.0 (M+1).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-c569514a6feb4a0bbba7ecab70f2fa5c
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08940724B2

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