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 1710961Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1710961
[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

Komponenten

3

Edukt 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

Produkt 1

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

Versuchsvorschrift

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%).

Quellen und Nachweise

ORD-Eintrag
ord-3ad29ae2aa1b48e7803a3d588a44c6f1
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07790729B2

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