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

HRID 1710966Notes

Reaction equation

HRID 1710966 reaction equation
FC1C=C(N)C=CC=1OC1C=CN=C2C=CSC=12.[F:19][C:20]1[CH:21]=[C:22]([NH:46][C:47]([NH:49][C:50](=[O:58])[CH2:51][C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)=[S:48])[CH:23]=[CH:24][C:25]=1[O:26][C:27]1[CH:32]=[CH:31][N:30]=[C:29]2[CH:33]=[C:34](C3C=CC(S(C)(=O)=O)=CC=3)[S:35][C:28]=12>>[F:19][C:20]1[CH:21]=[C:22]([NH:46][C:47]([NH:49][C:50](=[O:58])[CH2:51][C:52]2[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=2)=[S:48])[CH:23]=[CH:24][C:25]=1[O:26][C:27]1[CH:32]=[CH:31][N:30]=[C:29]2[CH:33]=[CH:34][S:35][C:28]=12

Participants

3

Reactant 2

HCID 58772875N-(3-Fluoro-4-(2-(4-(methylsulfonyl)phenyl)thieno[3,2-b]pyridin-7-yloxy)phenylcarbamothioyl)-2-phenylacetamideHCID 594244303-Fluoro-4-(thieno[3,2-b]pyridin-7-yloxy)aniline

Product 1

HCID 24901699N-(3-Fluoro-4-(thieno[3,2-b]pyridin-7-yloxy)phenylcarbamothioyl)-2-phenylacetamideYield 29%

Procedure

Starting from the amine 169 and following the procedure described above for the synthesis of compound 50 (scheme 10, example 55), title compound 170a was obtained in 29% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm: 12.46 (s, 1H), 11.81 (s, 1H), 8.52(d, J=5.2 Hz, 1H), 8.17(d, J=5.2 Hz, 1H), 8.01(dd, J=2.0 and 11.2 Hz, 1H), 7.60(d, J=5.2 Hz, 1H), 7.58-7.48 (m, 2H), 7.36-7.30 (m, 4H), 7.30-7.22 (m, 1H), 6.64(d, J=5.2 Hz, 1H), 3.82 (s, 2H). LRMS (M+1) 437.5 (100%).

Sources & evidence

ORD record
ord-ae8117732e764ed49db947f89d96307b
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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