tert-Butyl 4-(4-(7-(2-fluoro-4-(3-(2-phenylacetyl)thioureido)phenoxy)thieno[3,2-b]pyridine-2-yl)phenyl)piperazine-1-carboxylate → N-(3-Fluoro-4-(2-(4-(piperazin-1-yl)phenyl)thieno[3,2-b]pyridin-7-yloxy)phenylcarbamothioyl)-2-phenylacetamide di-hydrochloride

HRID 1710961Notes

Reaction equation

HRID 1710961 reaction equation
[ClH:1].FC1C=C(NC(NC(=O)CC2C=CC=CC=2)=S)C=CC=1OC1C=CN=C2C=C(C(NC[C@H]3CCNC3)=O)SC=12.[F:41][C:42]1[CH:76]=[C:75]([NH:77][C:78]([NH:80][C:81](=[O:89])[CH2:82][C:83]2[CH:88]=[CH:87][CH:86]=[CH:85][CH:84]=2)=[S:79])[CH:74]=[CH:73][C:43]=1[O:44][C:45]1[CH:50]=[CH:49][N:48]=[C:47]2[CH:51]=[C:52]([C:54]3[CH:59]=[CH:58][C:57]([N:60]4[CH2:65][CH2:64][N:63](C(OC(C)(C)C)=O)[CH2:62][CH2:61]4)=[CH:56][CH:55]=3)[S:53][C:46]=12>>[ClH:1].[ClH:1].[F:41][C:42]1[CH:76]=[C:75]([NH:77][C:78]([NH:80][C:81](=[O:89])[CH2:82][C:83]2[CH:84]=[CH:85][CH:86]=[CH:87][CH:88]=2)=[S:79])[CH:74]=[CH:73][C:43]=1[O:44][C:45]1[CH:50]=[CH:49][N:48]=[C:47]2[CH:51]=[C:52]([C:54]3[CH:55]=[CH:56][C:57]([N:60]4[CH2:65][CH2:64][NH:63][CH2:62][CH2:61]4)=[CH:58][CH:59]=3)[S:53][C:46]=12

Participants

3

Reactant 2

HCID 59424597tert-Butyl 4-(4-(7-(2-fluoro-4-(3-(2-phenylacetyl)thioureido)phenoxy)thieno[3,2-b]pyridine-2-yl)phenyl)piperazine-1-carboxylateHCID 86604177(S)-7-(2-Fluoro-4-(3-(2-phenylacetyl)thioureido)phenoxy)-N-(pyrrolidin-3-ylmethyl)thieno[3,2-b]pyridine-2-carboxamide hydrochloride

Product 1

HCID 86604176N-(3-Fluoro-4-(2-(4-(piperazin-1-yl)phenyl)thieno[3,2-b]pyridin-7-yloxy)phenylcarbamothioyl)-2-phenylacetamide di-hydrochlorideYield 21%

Procedure

Following the procedure described above for the synthesis of compound 137a (scheme 25, example 97) but substituting compound 135b for the compound 158, title compound 159 was obtained in 21% yield. 1H NMR (400 MHz, DMSO-d6) δ ppm: 12.48(s, 1H), 11.84 (s, 1H), 9.26(bs, 1H), 8.62(d, J=5.6 Hz, 1H), 8.05(d, J=12.0 Hz, 1H), 7.94 (s, 1H), 7.81(d, J=8.8 Hz, 2H), 7.62-7.55 (m, 2H), 7.37-7.31 (m, 4H), 7.31-7.24 (m, 1H), 7.10(d, J=8.8 Hz, 2H), 6.85(d, J=5.6 Hz, 1H), 3.83 (s, 2H), 3.58-3.51 (m, 4H), 3.26-3.18 (m, 4H). LRMS (M+1) 597.2 (100%).

Sources & evidence

ORD record
ord-3ad29ae2aa1b48e7803a3d588a44c6f1
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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