2-(2-Thienyl)ethanoyl isothiocyanate → N-(3-Fluoro-4-(thieno[3,2-b]pyridin-7-yloxy)phenylcarbamothioyl)-2-(thiophen-2-yl)acetamide

HRID 500837Notes

Reaction equation

HRID 500837 reaction equation
C(N1C2N=CN=C(OC3C=CC(NC(NC(=O)CC4C=CC=CC=4)=[S:26])=CC=3F)C=2C=C1)C1C=CC=CC=1.[F:38][C:39]1[CH:40]=[C:41]([NH:55][C:56]([NH:58][C:59](=[O:67])[CH2:60][C:61]2C=C[CH:64]=[CH:63][CH:62]=2)=[S:57])[CH:42]=[CH:43][C:44]=1[O:45][C:46]1[CH:51]=[CH:50][N:49]=[C:48]2[CH:52]=[CH:53][S:54][C:47]=12.S1C=CC=C1CC(N=C=S)=O>>[F:38][C:39]1[CH:40]=[C:41]([NH:55][C:56]([NH:58][C:59](=[O:67])[CH2:60][C:61]2[S:26][CH:64]=[CH:63][CH:62]=2)=[S:57])[CH:42]=[CH:43][C:44]=1[O:45][C:46]1[CH:51]=[CH:50][N:49]=[C:48]2[CH:52]=[CH:53][S:54][C:47]=12

Participants

4

Reactant 3

HCID 218903862-(2-Thienyl)ethanoyl isothiocyanateHCID 24901699N-(3-Fluoro-4-(thieno[3,2-b]pyridin-7-yloxy)phenylcarbamothioyl)-2-phenylacetamideHCID 866096601-(4-(7-Benzyl-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy)-3-fluorophenyl)-3-(2-phenylacetyl)thiourea

Product 1

HCID 86604181N-(3-Fluoro-4-(thieno[3,2-b]pyridin-7-yloxy)phenylcarbamothioyl)-2-(thiophen-2-yl)acetamideYield 9%

Procedure

Starting from the amine 169 (scheme 33), following the procedures described above for the synthesis of compound 170a (example 133) but replacing 2-phenylacetyl isothiocyanate with 2-(thiophen-2-yl)acetyl isothiocyanate, title compound 192b was obtained in 9% yield. Characterization of 192b is provided in table 18.

Sources & evidence

ORD record
ord-f5ce791137fe496fb67c796429e55fd0
Source dataset
uspto-grants-2010_08
Patent number
US07772247B2

Reaction notes

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