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tert-Butyl 2-(7-(2-fluoro-4-(3-(2-phenylacetyl)thioureido)phenoxy)thieno[3,2-b]pyridine-2-carboxamido)ethyl(methyl)carbamate → Hydrochloric Acid

HRID 1261251
Notes
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Reaction equation

HRID 1261251 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]
ParticipantsProcedureSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 59424483tert-Butyl 2-(7-(2-fluoro-4-(3-(2-phenylacetyl)thioureido)phenoxy)thieno[3,2-b]pyridine-2-carboxamido)ethyl(methyl)carbamateHCID 86604177(S)-7-(2-Fluoro-4-(3-(2-phenylacetyl)thioureido)phenoxy)-N-(pyrrolidin-3-ylmethyl)thieno[3,2-b]pyridine-2-carboxamide hydrochloride

Product 2

HCID 313Hydrochloric AcidHCID 866096597-(2-Fluoro-4-(3-(2-phenylacetyl)thioureido)phenoxy)-N-(2-(methylamino)ethyl)thieno[3,2-b]pyridine-2-carboxamide hydrochloride

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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08470850B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes