N1-(3-Fluoro-4-(2-(3-methoxy-4-(2-morpholinoethoxy)phenyl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-N2-(2-methoxyphenethyl)oxalamide → N1-(4-(2-(1-Ethyl-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenyl)-N2-(2-methoxyphenethyl)oxalamide

HRID 418649Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 418649
[F:1][C:2]1[CH:3]=[C:4]([NH:25][C:26](=[O:32])[C:27](OCC)=[O:28])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:15]=[C:16]([C:18]3[N:19]=[CH:20][N:21]([CH2:23][CH3:24])[CH:22]=3)[S:17][C:10]=12.FC1C=C(NC(=O)C([NH:71][CH2:72][CH2:73][C:74]2[CH:79]=[CH:78][CH:77]=[CH:76][C:75]=2[O:80][CH3:81])=O)C=CC=1OC1C=CN=C2C=C(C3C=CC(OCCN4CCOCC4)=C(OC)C=3)SC=12>>[CH2:23]([N:21]1[CH:22]=[C:18]([C:16]2[S:17][C:10]3[C:11](=[N:12][CH:13]=[CH:14][C:9]=3[O:8][C:7]3[CH:6]=[CH:5][C:4]([NH:25][C:26](=[O:32])[C:27]([NH:71][CH2:72][CH2:73][C:74]4[CH:79]=[CH:78][CH:77]=[CH:76][C:75]=4[O:80][CH3:81])=[O:28])=[CH:3][C:2]=3[F:1])[CH:15]=2)[N:19]=[CH:20]1)[CH3:24]

Komponenten

3

Edukt 2

HCID 16042167N1-(3-Fluoro-4-(2-(3-methoxy-4-(2-morpholinoethoxy)phenyl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-N2-(2-methoxyphenethyl)oxalamideHCID 58790366Ethyl 2-(3-fluoro-4-(2-(1-ethyl-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yloxy)phenylamino)-2-oxoacetate

Produkt 1

HCID 16042358N1-(4-(2-(1-Ethyl-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenyl)-N2-(2-methoxyphenethyl)oxalamideAusbeute 90 %

Versuchsvorschrift

Starting from the amino ester 142 and following the same procedure as described for the synthesis of compound 136 (example 52, scheme 40), title compound 141 was obtained as white solid in 90% yield. 1H NMR (DMSO-d6) δ (ppm): 11.04 (s, 1H), 9.06 (t, J=6.4 Hz, 1H), 8.43 (d, J=5.6 Hz, 1H), 8.02 (dd, J=2.4 and 12.8 Hz, 1H), 7.97 (d, J=1.2 Hz, 1H), 7.84-7.78 (m, 1H), 7.79 (d, J=1.2 Hz, 1H), 7.67 (s, 1H), 7.52 (t, J=5.2 Hz, 1H), 7.20 (td, J=1.6 and 8.0 Hz, 1H), 7.14 (dd, J=1.6 and 7.2 Hz, 1H), 6.96 (d, J=8.0 Hz, 1H), 6.87 (t, J=7.2 Hz, 1H), 6.58 (d, J=5.6 Hz, 1H), 4.06 (q, J=7.2 Hz, 2H), 3.79 (s, 3H), 3.42 (q, J=7.2 Hz, 2H), 2.82 (t, J=7.2 Hz, 2H), 1.40 (7.2 Hz, 3H). MS (m/z): 560.2 (M+H).

Quellen und Nachweise

ORD-Eintrag
ord-140feedb9e6a47a599c33e5c8f73e732
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093264B2

Notizen zur Reaktion

Wird geladen…