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
Reaction equation
[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]Participants
3
Reactant 2
Product 1
Procedure
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).
Sources & evidence
- ORD record
- ord-140feedb9e6a47a599c33e5c8f73e732
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08093264B2
Reaction notes
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