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 2193715Notes

Reaction equation

HRID 2193715 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

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

Product 1

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

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-289ee9a24f934eb58ace8212bd7ac3d6
Source dataset
uspto-grants-2012_12
Patent number
US08329726B2

Reaction notes

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