tert-Butyl 2-(7-(2-fluoro-4-(3-(2-phenylacetyl)thioureido)phenoxy)thieno[3,2-b]pyridine-2-carboxamido)ethyl(methyl)carbamate → Hydrochloric Acid
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:71]=[C:70]([NH:72][C:73]([NH:75][C:76](=[O:84])[CH2:77][C:78]2[CH:83]=[CH:82][CH:81]=[CH:80][CH:79]=2)=[S:74])[CH:69]=[CH:68][C:43]=1[O:44][C:45]1[CH:50]=[CH:49][N:48]=[C:47]2[CH:51]=[C:52]([C:54]([NH:56][CH2:57][CH2:58][N:59](C)[C:60](=O)OC(C)(C)C)=[O:55])[S:53][C:46]=12>>[ClH:1].[F:41][C:42]1[CH:71]=[C:70]([NH:72][C:73]([NH:75][C:76](=[O:84])[CH2:77][C:78]2[CH:79]=[CH:80][CH:81]=[CH:82][CH:83]=2)=[S:74])[CH:69]=[CH:68][C:43]=1[O:44][C:45]1[CH:50]=[CH:49][N:48]=[C:47]2[CH:51]=[C:52]([C:54]([NH:56][CH2:57][CH2:58][NH:59][CH3:60])=[O:55])[S:53][C:46]=12.[ClH:1]Participants
4
Reactant 2
Product 2
Procedure
Following the procedure described above for the synthesis of 137a but replacing compound 135b with compound 138, title compound 137b was obtained as an HCl salt in 65% yield 1H NMR (400 MHz, DMSO-d6 ppm: 12.49(s, 1H), 11.83(s, 1H), 9.39(t, J=5.2Hz, 1H), 8.80(bs, 1H), 8.62(d, J=5.6 Hz, 1H), 8.39(s, 1H), 8.04(d, J=11.6 Hz, 1H), 7.97(bs, 1H), 7.58-7.50(m, 2H), 7.37-7.31(m, 4H), 7.31-7.24(m, 1H), 6.80(d, J=5.6 Hz, 1H), 3.78-3.71(m, 0.5H), 3.61(q, J=6.0 Hz, 1H), 3.21-3.24(m, 0.5H), 3.18-3.04(m, 2H), 2.60 (t, J=4.8 Hz, 2H).
Sources & evidence
- ORD record
- ord-3ad3d1af9d834191a9937849816fbcf7
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08470850B2
Reaction notes
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