4-(2-(4-(2-Morpholinoethoxy)phenyl)thieno[3,2-b]pyridin-7-yloxy)benzenamine → N-(4-(2-(4-(2-Morpholinoethoxy)phenyl)thieno[3,2-b]pyridin-7-yloxy)phenylcarbamothioyl)-2-phenylacetamide

HRID 1261285Notes

Reaction equation

HRID 1261285 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[S:24][C:23]4[C:18](=[N:19][CH:20]=[CH:21][C:22]=4[O:25][C:26]4[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][CH:27]=4)[CH:17]=3)=[CH:12][CH:11]=2)[CH2:3][CH2:2]1.FC1C=C(N[C:66]([NH:68][C:69](=[O:77])[CH2:70][C:71]2[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=2)=[S:67])C=CC=1OC1C=CN=C2C=C(C3C=CC=C(OCCN4CCOCC4)C=3)SC=12>>[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[S:24][C:23]4[C:18](=[N:19][CH:20]=[CH:21][C:22]=4[O:25][C:26]4[CH:27]=[CH:28][C:29]([NH:32][C:66]([NH:68][C:69](=[O:77])[CH2:70][C:71]5[CH:72]=[CH:73][CH:74]=[CH:75][CH:76]=5)=[S:67])=[CH:30][CH:31]=4)[CH:17]=3)=[CH:12][CH:11]=2)[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 594244154-(2-(4-(2-Morpholinoethoxy)phenyl)thieno[3,2-b]pyridin-7-yloxy)benzenamineHCID 86604178N-(3-Fluoro-4-(2-(3-(2-morpholinoethoxy)phenyl)thieno[3,2-b]pyridin-7-yloxy)phenylcarbamothioyl)-2-phenylacetamide

Product 1

HCID 59424506N-(4-(2-(4-(2-Morpholinoethoxy)phenyl)thieno[3,2-b]pyridin-7-yloxy)phenylcarbamothioyl)-2-phenylacetamideYield 30%

Procedure

Starting from the compound 202 and following the procedure described above for the compound 163a (scheme 31), title compound 203 was obtained in 30% yield. 1H NMR (400 MHz, DMSO-d6 δ ppm: 12.38 (s, 1H), 11.73 (s, 1H), 8.47 (d, 1H, J=5.5 Hz), 7.90 (s, 1H), 7.79 (s, 2H, J=9.0), 7.36 (d, 2H, J=9.0 Hz), 7.43-7.27 (m, 7H), 7.05 (d, 2H, J=9.0 Hz), 6.63 (d, 1H, J=5.3 Hz), 4.15 (t, 2H, J=5.6 Hz), 3.82 (s, 2H), 3.58 (t, 4H, J=4.6 Hz), 2.71 (t, 2H, J=5.7 Hz), 2.51-2.46 (m, 4H). LRMS (M+1) 625.2 (100%).

Sources & evidence

ORD record
ord-1fbeb2ad81e04f089adac1410389ae0b
Source dataset
uspto-grants-2013_06
Patent number
US08470850B2

Reaction notes

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