4-(Chloromethyl)-1,3-thiazole → 2-Hydroxy-N-{2-[(4-{[3-methyl-4-(1,3-thiazol-4-ylmethoxy)phenyl]amino}quinazolin-5-yl)oxy]ethyl}acetamide

HRID 1864297Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1864297
Cl[CH2:2][C:3]1[N:4]=[CH:5][S:6][CH:7]=1.[OH:8][CH2:9][C:10]([NH:12][CH2:13][CH2:14][O:15][C:16]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:17]=1[C:18]([NH:26][C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[C:29]([CH3:34])[CH:28]=1)=[N:19][CH:20]=[N:21]2)=[O:11]>>[OH:8][CH2:9][C:10]([NH:12][CH2:13][CH2:14][O:15][C:16]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:17]=1[C:18]([NH:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH2:2][C:3]3[N:4]=[CH:5][S:6][CH:7]=3)=[C:29]([CH3:34])[CH:28]=1)=[N:19][CH:20]=[N:21]2)=[O:11]

Komponenten

3

Edukt 2

HCID 27632904-(Chloromethyl)-1,3-thiazoleHCID 690609102-hydroxy-N-[2-({4-[(4-hydroxy-3-methylphenyl)amino]quinazolin-5-yl}oxy)ethyl]acetamide

Produkt 1

HCID 113747212-Hydroxy-N-{2-[(4-{[3-methyl-4-(1,3-thiazol-4-ylmethoxy)phenyl]amino}quinazolin-5-yl)oxy]ethyl}acetamideAusbeute 21 %

Versuchsvorschrift

The procedure described in Example 3 was repeated using 4-(chloromethyl)-1,3-thiazole and 2-hydroxy-N-[2-({4-[(4-hydroxy-3-methylphenyl)amino]quinazolin-5-yl}oxy)ethyl]acetamide (obtained as described in Example 79, preparation of starting materials) to give the title compound as a yellow solid in 21% yield; NMR spectrum (DMSO-d6) 2.20 (s, 3H), 3.71 (q, 2H), 3.77 (d, 2H), 4.38 (t, 2H), 5.23 (s, 2H), 5.49 (t, 1H), 7.08 (d, 1H), 7.13 (d, 1H), 7.32 (d, 1H), 7.44 (d, 1H), 7.57 (dd, 1H), 7.69 (t, 1H), 7.77 (d, 1H), 8.17 (t, 1H), 8.42 (s, 1H), 9.14 (d, 1H), 9.77 (s, 1H); Mass spectrum MH+ 466.

Quellen und Nachweise

ORD-Eintrag
ord-bb0d35116cc04be4bff9033e9f9d1583
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07625908B2

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