3-Chloro-4-(1-methyl-1-pyridin-2-ylethoxy)aniline → N-{2-[(4-{[3-Chloro-4-(1-methyl-1-pyridin-2-ylethoxy)phenyl]amino}quinazolin-5-yl)oxy]ethyl}-N-methylacetamide

HRID 1864358Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1864358
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[O:12][CH2:13][CH2:14][N:15]([CH3:19])[C:16](=[O:18])[CH3:17])[N:5]=[CH:4][N:3]=1.[Cl:20][C:21]1[CH:22]=[C:23]([CH:25]=[CH:26][C:27]=1[O:28][C:29]([CH3:37])([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=1)[CH3:30])[NH2:24]>>[Cl:20][C:21]1[CH:22]=[C:23]([NH:24][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][C:10]=3[O:12][CH2:13][CH2:14][N:15]([CH3:19])[C:16](=[O:18])[CH3:17])[N:5]=[CH:4][N:3]=2)[CH:25]=[CH:26][C:27]=1[O:28][C:29]([CH3:30])([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=1)[CH3:37]

Komponenten

3

Edukt 2

HCID 690590593-Chloro-4-(1-methyl-1-pyridin-2-ylethoxy)anilineHCID 86615689N-{2-[(4-Chloroquinazolin-5-yl)oxy]ethyl}-N-methylacetamide

Produkt 1

HCID 57974354N-{2-[(4-{[3-Chloro-4-(1-methyl-1-pyridin-2-ylethoxy)phenyl]amino}quinazolin-5-yl)oxy]ethyl}-N-methylacetamideAusbeute 31 %

Versuchsvorschrift

The procedure described in Example 126 was repeated using N-{2-[(4-chloroquinazolin-5-yl)oxy]ethyl}-N-methylacetamide (obtained as described in Example 126, preparation of starting materials, 47 mg, 0.170 mmol) and 3-chloro-4-(1-methyl-1-pyridin-2-ylethoxy)aniline (49 mg, 0.187 mmol) to give the title compound in 31% yield; NMR Spectrum (DMSO-d6, 400 MHz, 373K) 1.75 (s, 6H), 1.92 (s, 3H), 2.94 (s, 3H), 3.88 (t, 2H), 4.47 (t, 2H), 6.62 (d, 1H), 7.16 (d, 1H), 7.31 (ddd, 1H), 7.35 (d, 1H), 7.39 (dd, 1H), 7.70 (dd, 1H), 7.75 (dd, 1H), 7.83 (ddd, 1H), 7.99 (d, 1H), 8.46 (s, 1H), 8.58 (dd, 1H), 9.70 (s, 1H); Mass spectrum MH+ 506.0.

Quellen und Nachweise

ORD-Eintrag
ord-b6fc1b8c00244cdb87466758e460f02b
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07625908B2

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